Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2007(14): 2065-2092
DOI: 10.1055/s-2007-983747
DOI: 10.1055/s-2007-983747
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Organocatalytic Enantioselective Michael and Hetero-Michael Reactions
Further Information
Received
12 April 2007
Publication Date:
03 July 2007 (online)
Publication History
Publication Date:
03 July 2007 (online)
Abstract
The enantioselective methods reported to date for carrying out conjugate additions of carbon- and heteroatom-centered nucleophiles to electron-deficient olefins, using small chiral organic molecules as catalysts, are reviewed.
1 Introduction
2 Organocatalytic Enantioselective Michael Reactions
2.1 Reactions Proceeding via Enamine Intermediates
2.2 Reactions Proceeding via Iminium Intermediates
2.3 Reactions Proceeding via Enamine and Iminium Intermediates
2.4 Reactions Catalyzed by Chiral Thioureas
2.5 Reactions Catalyzed by Cinchona Alkaloids
2.6 Reactions under Phase-Transfer Conditions
2.7 Reactions Catalyzed by Other Organocatalysts
3 Organocatalytic Enantioselective Conjugate Friedel-Crafts Alkylations
4 Organocatalytic Enantioselective Conjugate Hydrogen-Transfer Reactions
5 Organocatalytic Enantioselective Hetero-Michael Reactions
5.1 Sulfa-Michael Reactions
5.2 Aza-Michael Reactions
5.3 Oxa-Michael Reactions
5.4 Phospha-Michael Reactions
6 Miscellaneous Organocatalytic Enantioselective Conjugate Additions
7 Conclusions and Outlook
Key words
asymmetric catalysis - asymmetric synthesis - Michael additions - organocatalysis
- General reviews:
-
1a
Seayad J.List B. Org. Biomol. Chem. 2005, 3: 719 -
1b
Dalko PI.Moisan L. Angew. Chem. Int. Ed. 2004, 43: 5138 - See also:
-
1c
Berkessel A.Groger H. In Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis Wiley-VCH; Weinheim: 2005. - 2
Perlmutter P. Conjugate Addition Reactions in Organic Synthesis Pergamon Press; Oxford: 1992. - 3 For a recent review, see:
Guo H.-C.Ma J.-A. Angew. Chem. Int. Ed. 2006, 45: 354 - During the preparation of this manuscript, two reviews appeared covering this subject:
-
4a
Tsogoeva SB. Eur. J. Org. Chem. 2007, 1701 -
4b
Almaºi D.Alonso DA.Nájera C. Tetrahedron: Asymmetry 2007, 18: 299 - For some reviews on asymmetric aminocatalysis, see:
-
5a
List B. Chem. Commun. 2006, 819 -
5b
Jarvo ER.Miller SD. Tetrahedron 2002, 58: 2481 -
5c
List B. Tetrahedron 2002, 58: 5573 -
6a For a general review on asymmetric conjugate additions to nitroalkenes, see:
Berner OM.Tedeschi L.Enders D. Eur. J. Org. Chem. 2002, 1877 -
6b For a review focused on amine-catalyzed reactions see:
Sulzer-Mosse S.Alexakis A. Chem. Commun. 2007, in press; DOI: 10.1039/b701216k -
7a
Betancort JM.Sakthivel K.Thayumanavan R.Tanaka F.Barbas CF. Synthesis 2004, 1509 -
7b
Enders D.Seki A. Synlett 2002, 26 -
7c
List B.Pojarliev P.Martin HJ. Org. Lett. 2001, 3: 2423 -
8a
Cobb AJA.Longbottom DA.Shaw DM.Ley SL. Chem. Commun. 2004, 1808 -
8b For a computational study explaining the role of this catalyst in the reaction, see:
Arnó M.Zaragozá RJ.Domingo LR. Tetrahedron: Asymmetry 2007, 18: 157 - 9
Mitchell CET.Cobb AJA.Ley SV. Synlett 2005, 611 - 10
Ishii T.Fujioka S.Sekiguchi Y.Kotsuki H. J. Am. Chem. Soc. 2004, 126: 9558 -
11a
Pansare SV.Pandya K. J. Am. Chem. Soc. 2006, 128: 9624 -
11b For another triamine-catalyzed example, see:
Zhu M.-K.Cun L.-F.Mi A.-Q.Jiang Y.-Z.Gong L.-Z. Tetrahedron: Asymmetry 2006, 17: 491 -
12a
Xu Y.Córdova A. Chem. Commun. 2006, 460 -
12b For a similar dipeptide-catalyzed version, see:
Wu Y.Zou W.Sundén H.Ibrahem I.Córdova A. Adv. Synth. Catal. 2006, 348: 418 -
12c For the use of a proline-valine dipeptide, see:
Martin HJ.List B. Synlett 2003, 1901 -
13a
Yan Z.-Y.Niu Y.-N.Wei H.-L.Wu L.-Y.Zhao Y.-B.Liang Y.-M. Tetrahedron: Asymmetry 2006, 17: 3288 -
13b
Luo SD.Xu H.Mi X.Li J.Zheng X.Cheng J.-P. J. Org. Chem. 2006, 71: 9244 -
13c
Almaºi D.Alonso DA.Nájera C. Tetrahedron: Asymmetry 2006, 17: 2064 - 14
Betancort JM.Barbas CF. Org. Lett. 2001, 3: 3737 - 15
Mase N.Thayumanavan R.Tanaka F.Barbas CF. Org. Lett. 2004, 6: 2527 -
16a
Andrey O.Alexakis A.Tomassini A.Bernardinelli G. Adv. Synth. Catal. 2004, 346: 1147 -
16b For a related 3,3′-bimorpholine catalyst used in this reaction, see:
Mosse S.Laars M.Kriis K.Kanger T.Alexakis A. Org. Lett. 2006, 8: 2559 - 17
Mosse S.Alexakis A. Org. Lett. 2006, 8: 3577 - 18
Barros MT.Phillips AMF. Eur. J. Org. Chem. 2007, 178 - 19 For a review on the use of diarylprolinol silyl ethers as organocatalysts, see:
Palomo C.Mielgo A. Angew. Chem. Int. Ed. 2006, 45: 7876 - 20
Hayashi Y.Gotoh H.Hayashi T.Shoji M. Angew. Chem. Int. Ed. 2005, 44: 4212 - 21
Wang W.Wang J.Li H. Angew. Chem. Int. Ed. 2005, 44: 1369 -
22a
Wang J.Li H.Lou B.Zu L.Guo H.Wang W. Chem. Eur. J. 2006, 12: 4321 -
22b For the use of a modified derivative, see:
Diez D.Gil MJ.Moro RF.Marcos IS.Garcia P.Basabe P.Garrido NM.Broughton HB.Urones JG. Tetrahedron 2007, 63: 740 - 23
Seebach D.Golinski J. Helv. Chim. Acta 1981, 64: 1413 - 24
Palomo C.Vera S.Mielgo A.Gómez-Bengoa E. Angew. Chem. Int. Ed. 2006, 45: 5984 - 25
Reyes E.Vicario JL.Badia D.Carrillo L. Org. Lett. 2006, 8: 6135 - 26
Andrey O.Vidonne A.Alexakis A. Tetrahedron Lett. 2003, 44: 7901 - 27
Andrey O.Alexakis A.Bernardinelli G. Org. Lett. 2003, 5: 2559 - 28
Albertshofer K.Thayumanavan R.Utsumi N.Tanaka F.Barbas CF. Tetrahedron Lett. 2007, 48: 693 - 29
Enders D.Chow S. Eur. J. Org. Chem. 2006, 4578 - 30
McCooey SM.Connon SJ. Org. Lett. 2007, 9: 599 - 31
Clarke ML.Fuentes JA. Angew. Chem. Int. Ed. 2007, 46: 930 -
32a
Mase N.Watanabe K.Yoda H.Takabe K.Tanaka F.Barbas CF. J. Am. Chem. Soc. 2006, 128: 4966 -
32b For another recent example of a Michael reaction in water, see:
Singh V.Singh VK. Org. Lett. 2007, 9: 1117 - 33
Zu L.Li H.Wang J.Yu X.Wang W. Tetrahedron Lett. 2006, 47: 5131 - 34
Zu L.Wang J.Li H.Wang W. Org. Lett. 2006, 8: 3077 -
35a
Luo S.Mi X.Zhang L.Liu S.Xu H.Cheng J.-P. Angew. Chem. Int. Ed. 2006, 45: 3093 -
35b
Luo S.Mi X.Liu H.Cheng J.-P. Chem. Commun. 2006, 3687 -
35c For another related example, see:
Xu D.Luo S.Yue H.Wang L.Xu Z. Synlett 2006, 2569 - 36
Li Y.Liu X.-Y.Zhao G. Tetrahedron: Asymmetry 2006, 17: 2034 - 37
Franzén J.Marigo M.Fielenbach D.Wabnitz TC.Kjaersgaard A.Jørgensen KA. J. Am. Chem. Soc. 2005, 127: 18296 - 38
Melchiorre P.Jørgensen KA. J. Org. Chem. 2003, 68: 4151 -
39a
Chi Y.Gellman SH. Org. Lett. 2005, 7: 4253 -
39b
Peelen TJ.Chi Y.Gellman SH. J. Am. Chem. Soc. 2005, 127: 11598 -
40a
Hechavarria Fonseca MT.List B. Angew. Chem. Int. Ed. 2004, 43: 3958 -
40b For a related work using a proline-derived aniline as catalyst, see:
Kikuchi M.Inagaki T.Nishiyama H. Synlett 2007, 1075 - 41
Hayashi Y.Gotoh H.Tamura T.Yamaguchi H.Masui R.Shoji M. J. Am. Chem. Soc. 2005, 127: 16028 - 42
Wang W.Li H.Zu L.Wang W. Adv. Synth. Catal. 2006, 348: 425 - 43
Mossé S.Alexakis A. Org. Lett. 2005, 7: 4361 - 44
Zhao G.-L.Xu Y.Sundén H.Eriksson L.Sayah M.Córdova A. Chem. Commun. 2007, 734 - 45
Cao C.-L.Sun X.-L.Zhou J.-L.Tang Y. J. Org. Chem. 2007, 72: 4073 - 46
Kawara A.Taguchi T. Tetrahedron Lett. 1994, 35: 8805 - 47
Halland N.Aburel PS.Jørgensen KA. Angew. Chem. Int. Ed. 2003, 42: 661 -
48a
Halland N.Hansen T.Jørgensen KA. Angew. Chem. Int. Ed. 2003, 42: 4955 - For other following organocatalytic syntheses of warfarin, see:
-
48b
Xie J.-S.Yue L.Chen W.Du W.Zhu J.Deng J.-G.Chen Y.-C. Org. Lett. 2007, 9: 413 -
48c
Kim H.Yen C.Preston P.Chin J. Org. Lett. 2006, 8: 5239 - 49
Knudsen KR.Mitchell CET.Ley SV. Chem. Commun. 2006, 66 - 50
Brandau S.Landa A.Franzén J.Marigo M.Jørgensen KA. Angew. Chem. Int. Ed. 2006, 45: 4305 - 51
Hanessian S.Pham V. Org. Lett. 2000, 2: 2975 - 52
Hanessian S.Shao Z.Warrier JS. Org. Lett. 2006, 8: 4787 -
53a
Tsogoeva SB.Jagtap SB.Ardemasova ZA. Tetrahedron: Asymmetry 2006, 17: 989 -
53b
Tsogoeva SB.Jagtap SB.Ardemasova ZA.Kalikhevich VN. Eur. J. Org. Chem. 2004, 4014 -
53c For a related peptide-mediated Michael reaction of nitroalkanes to cycloalken-ones, see:
Tsogoeva SB.Jagtap SB. Synlett 2004, 2624 - 54
Hojabri L.Hartikka A.Moghaddam FM.Arvidsson PI. Adv. Synth. Catal. 2007, 349: 740 - 55
Halland N.Hazell RG.Jørgensen KA. J. Org. Chem. 2002, 67: 8331 - 56
Prieto A.Halland N.Jørgensen KA. Org. Lett. 2005, 7: 3897 -
57a
Brown SP.Goodwin NC.MacMillan DWC. J. Am. Chem. Soc. 2003, 125: 1192 -
57b For the use of these conditions in reaction of acyclic silyl enol ethers, see:
Wang W.Li H.Wang J. Org. Lett. 2005, 7: 1637 - 58
Xie J.-W.Yue L.Xue D.Ma X.-L.Chen Y.-C.Wu Y.Zhu J.Deng J.-G. Chem. Commun. 2006, 1563 - 59
Xie J.-W.Chen W.Li R.Zeng M.Du W.Yue L.Chen Y.-C.Wu Y.Zhu J.Deng J.-G. Angew. Chem. Int. Ed. 2007, 46: 389 - 60
Enders D.Grondal C.Hüttl MRM. Angew. Chem. Int. Ed. 2007, 46: 1570 - 61
Bui T.Barbas CF. Tetrahedron Lett. 2000, 41: 6951 -
62a
Halland N.Aburel PS.Jørgensen KA. Angew. Chem. Int. Ed. 2004, 43: 1273 -
62b
Pulkkinen J.Aburel PS.Halland N.Jørgensen KA. Adv. Synth. Catal. 2004, 346: 1077 -
62c For a related work, see:
Gryko D. Tetrahedron: Asymmetry 2005, 16: 1377 - 63
Carlone A.Marigo M.North C.Landa A.Jørgensen KA. Chem. Commun. 2006, 4928 - 64
Marigo M.Bertelsen S.Landa A.Jørgensen KA. J. Am. Chem. Soc. 2006, 128: 5475 - 65
Zu L.Li H.Xie H.Wang J.Jiang W.Yang Y.Wang W. Angew. Chem. Int. Ed. 2007, 46: 3732 - 66
Enders D.Hüttl MRM.Grondal C.Raabe G. Nature 2006, 441: 861 - 67
Carlone A.Cabrera S.Marigo M.Jørgensen KA. Angew. Chem. Int. Ed. 2007, 46: 1101 -
68a
Hong B.-C.Wu MF.Tseng H.-C.Liao J.-H. Org. Lett. 2006, 8: 2217 -
68b For a related stoichiometric version, see:
Bench BJ.Liu C.Evett CR.Watanabe CMH. J. Org. Chem. 2006, 71: 9458 -
68c For a proline-catalyzed formal [3+3]-cycloaddition reaction between 5-methyl-3,4-dihydro-2H-pyrrole and cyclopenatenone, see:
Movassaghi M.Chen B. Angew. Chem. Int. Ed. 2007, 46: 565 -
69a
Akiyama T.Itoh J.Fuchibe J. Adv. Synth. Catal. 2006, 348: 999 -
69b
Pihko P. Angew. Chem. Int. Ed. 2004, 43: 2062 -
69c
Schreiner PN. Chem. Soc. Rev. 2003, 32: 289 -
70a
Taylor MS.Jacobsen EN. Angew. Chem. Int. Ed. 2006, 45: 1520 -
70b
Connon SJ. Chem. Eur. J. 2006, 12: 5418 -
70c
Takemoto Y. Org. Biomol. Chem. 2005, 3: 4299 -
71a
Okino T.Hoashi Y.Furukawa T.Xu X.Takemoto Y. J. Am. Chem. Soc. 2005, 127: 119 -
71b
Okino T.Hoashi Y.Takemoto Y. J. Am. Chem. Soc. 2003, 125: 12672 -
71c For a related thiourea catalysts incorporating a binaphthylamine backbone, see:
Wang J.Li H.Duan W.Zu L.Wang W. Org. Lett. 2005, 7: 4713 -
71d For a polymer-supported version, see:
Miyabe H.Tuchida S.Yamauchi M.Takemoto Y. Synthesis 2006, 3295 -
72a
Hamza A.Schubert G.Soós T.Pápai I. J. Am. Chem. Soc. 2006, 128: 13151 -
72b
Zhu R.Zhang D.Wu J.Liu C. Tetrahedron: Asymmetry 2006, 17: 1611 - 73
Tsogoeva SB.Yalalov DA.Hateley MJ.Weckbecker C.Hutchamacher K. Eur. J. Org. Chem. 2005, 4995 - 74
Liu K.Cui H.-F.Nie J.Dong K.-Y.Li X.-J.Ma J.-A. Org. Lett. 2007, 9: 923 - 75
Cao C.-L.Ye M.-C.Sun X.-L.Tang Y. Org. Lett. 2006, 8: 2901 - 76
Huang H.-B.Jacobsen EN. J. Am. Chem. Soc. 2006, 128: 7170 - 77
Cao Y.-J.Lu H.-H.Lai Y.-Y.Lu L.-Q.Xiao W.-J. Synthesis 2006, 3795 -
78a
Tsogoeva SB.Wei S.-W. Chem. Commun. 2006, 1451 -
78b See also:
Yalalov DA.Tsogoeva SB.Schmatz S. Adv. Synth. Catal. 2006, 348: 826 - 79
Lalonde MP.Chen Y.Jacobsen EN. Angew. Chem. Int. Ed. 2006, 26: 6366 - 80
Dixon DJ.Richardson RD. Synlett 2006, 81 -
81a
Inokuma T.Hoashi Y.Takemoto Inokuma T.Hoashi Y.Takemoto K. J. Am. Chem. Soc. 2006, 128: 9423 -
81b
Hoashi Y.Okino T.Takemoto Y. Angew. Chem. Int. Ed. 2005, 44: 4032 -
82a
Liu T.-Y.Li R.Chai Q.Long J.Li B.-J.Wu Y.Ding L.-S.Chen Y.-C. Chem. Eur. J. 2007, 13: 319 -
82b For the same reaction using vinyl sulfones, see:
Liu T.-Y.Long J.Li B.-J.Jiang L.Li R.Wu Y.Ding L.-S.Chen Y.-C. Org. Biomol. Chem. 2006, 4: 2097 - For some reviews, see:
-
83a
Marcelli T.van Maarseveen JH.Hiemstra H. Angew. Chem. Int. Ed. 2006, 45: 7496 -
83b
Dalaigh CO. Synlett 2005, 875 -
83c
Hoffmann H.Martin R.Frackenpohl J. Eur. J. Org. Chem. 2004, 4293 -
83d
Tian S.-K.Chen Y.Hang J.Tang L.McDaid P.Deng L. Acc. Chem. Res. 2004, 37: 621 -
83e
Yoon TP.Jacobsen EN. Science 2003, 299: 1691 -
83f
Kacprzak K.Gawroń J. Synthesis 2001, 961ski -
84a
Wynberg H.Helder R. Tetrahedron Lett. 1975, 4057 - See also:
-
84b
Hermann K.Wynberg H. J. Org. Chem. 1979, 44: 2238 -
84c
Hiemstra H.Wynberg H. J. Am. Chem. Soc. 1981, 103: 417 - For some examples on the use of polymer-supported cinchone catalysts:
-
84d
Alvarez R.Hourdin M.-A.Cavé C.d’Angelo J.Chaminade P. Tetrahedron Lett. 1999, 40: 7091 -
84e
Kobayashi N.Iwai K. J. Am. Chem. Soc. 1978, 100: 7071 - See, for example:
-
85a
Sera A.Takagi K.Katayama H.Yamada H. J. Org. Chem. 1988, 53: 1157 -
85b
Trost BM.Shuey CD.Di Ninno F.McElvain SS. J. Am. Chem. Soc. 1979, 101: 1284 -
85c
Latvala A.Stanchev S.Linden A.Hesse M. Tetrahedron: Asymmetry 1992, 4: 173 - 86
Li H.Wang Y.Tang L.Deng L. J. Am. Chem. Soc. 2004, 126: 9906 - 87
Li H.Wang Y.Tang L.Wu F.Liu X.Guo C.Foxman BM.Deng L. Angew. Chem. Int. Ed. 2005, 44: 105 - 88
Wu F.Li H.Hong R.Deng L. Angew. Chem. Int. Ed. 2006, 45: 947 - 89
Wu F.Hong R.Khan J.Liu X.Deng L. Angew. Chem. Int. Ed. 2006, 45: 4301 - 90
Li H.Song J.Liu X.Deng L. J. Am. Chem. Soc. 2005, 127: 8948 - 91
Wang Y.Liu X.Deng L. J. Am. Chem. Soc. 2006, 128: 3928 - 92
Bartoli G.Bosco M.Carlone A.Cavalli A.Locatelli M.Mazzanti A.Ricci P.Sambri L.Melchiorre P. Angew. Chem. Int. Ed. 2006, 45: 4966 - 93
Wang J.Li H.Zu L.Jiang W.Wang W. Adv. Synth. Catal. 2006, 348: 2047 - 94
Bella M.Jørgensen KA. J. Am. Chem. Soc. 2004, 126: 5672 -
95a
Papageorgiou CD.Cubillo de Dios MA.Ley SV.Gaunt MJ. Angew. Chem. Int. Ed. 2004, 43: 4641 -
95b
Papageorgiou CD.Ley SV.Gaunt MJ. Angew. Chem. Int. Ed. 2003, 42: 828 -
95c For a recent example using methylidenemalononitriles as acceptors, see:
Kojima S.Suzuki M.Watanabe A.Ohkata K. Tetrahedron Lett. 2006, 47: 9061 -
95d For an example using 2-bromocyclo-alkenones as electrophiles, see:
Arai S.Nakayama K.Ishida T.Shioiri T. Tetrahedron Lett. 1999, 40: 4215 -
95e For a related 2a-catalyzed version, see:
Hansen H.Longbottom DA.Ley SV. Chem. Commun. 2006, 4838 -
96a
Johansson CCC.Bremeyer N.Ley SV.Owen DR.Smith SC.Gaunt MJ. Angew. Chem. Int. Ed. 2006, 45: 6024 -
96b
Bremeyer N.Smith SC.Ley SV.Gaunt MJ. Angew. Chem. Int. Ed. 2004, 43: 2681 -
97a
Xue D.Chen Y.-C.Wang Q.-W.Cun L.-F.Zhu J.Deng J.-G. Org. Lett. 2005, 7: 5293 -
97b
Poulsen TB.Bell M.Jørgensen KA. Org. Biomol. Chem. 2006, 4: 63 - 98
Bell M.Frisch K.Jørgensen KA. J. Org. Chem. 2006, 71: 5407 -
99a
Ye J.Dixon DJ.Hynes PS. Chem. Commun. 2005, 4481 -
99b See also:
Hynes PS.Stranges D.Stupple PA.Guarna A.Dixon DJ. Org. Lett. 2007, 9: 2107 -
100a
McCooey SH.Connon SJ. Angew. Chem. Int. Ed. 2005, 44: 6367 - For a similar reaction involving cyclo-propane formation, see:
-
100b
McCooey SH.McCabe T.Connon SJ. J. Org. Chem. 2006, 71: 7494 - For further progresses expanding the scope of this reaction using catalyst 37a, see
-
100c
Wang J.Li H.Zu L.Jiang W.Xie H.Duan W.Wang W. J. Am. Chem. Soc. 2006, 128: 12652 -
100d
Gu C.Liu L.Sui Y.Zhao J.-L.Wang D.Chen Y.-J. Tetrahedron: Asymmetry 2007, 18: 455 - 101
Vakulya B.Varga S.Csámpai A.Soos T. Org. Lett. 2005, 7: 1967 - 102
Wang B.Wu F.Wang Y.Liu X.Deng L. J. Am. Chem. Soc. 2007, 129: 768 -
103a
Ooi T.Maruoka K. Angew. Chem. Int. Ed. 2007, 46: 4222 -
103b
Maruoka K.Ooi T.Kano T. Chem. Commun. 2007, 1487 -
103c
Lygo B.Andrews BI. Acc. Chem. Res. 2004, 37: 518 -
103d
Maruoka K.Ooi T. Chem. Rev. 2003, 103: 3013 -
103e
Nájera C. Synlett 2002, 1388 - 104
Ooi T.Maruoka K. Acc. Chem. Res. 2004, 37: 526 -
105a
Ooi T.Fujioka S.Maruoka K. J. Am. Chem. Soc. 2004, 126: 11790 -
105b
Ooi T.Takada S.Fujioka S.Maruoka K. Org. Lett. 2005, 7: 5143 - 106
Ooi T.Takada S.Doda K.Maruoka K. Angew. Chem. Int. Ed. 2006, 45: 7606 - 107
Ooi T.Doda K.Maruoka K. J. Am. Chem. Soc. 2003, 125: 9022 - 108
Wang X.Kitamura M.Maruoka K. J. Am. Chem. Soc. 2007, 129: 1038 - 109
Ooi T.Ohara D.Fukumoto K.Maruoka K. Org. Lett. 2005, 7: 3195 - 110
Lee Y.-J.Lee J.Kim M.-J.Jeong B.-S.Lee J.-H.Kim TS.Lee J.Ku J.-M.Sew S.Park H. Org. Lett. 2005, 7: 3207 -
111a
Shibuguchi T.Mihara H.Kuramochi A.Saturaba S.Ohshima T.Shibasaki M. Angew. Chem. Int. Ed. 2006, 45: 4635 -
111b
Ohshima T.Gnanadesikan V.Shibuguchi T.Fukuta Y.Nemoto T.Shibasaki M. J. Am. Chem. Soc. 2003, 125: 11206 -
111c For the use of other tartrate-derived catalysts, see:
Arai S.Tsuji R.Nishida A. Tetrahedron Lett. 2002, 43: 9535 -
112a
Zhang F.-Y.Corey E. J. Org. Lett. 2001, 3: 639 -
112b
Zhang F.-J.Corey EJ. Org. Lett. 2000, 2: 1097 -
112c
Corey EJ.Zhang F.-J. Org. Lett. 2000, 2: 4257 -
112d For an example of Michael reaction of malonates and chalcones, see:
Kim DY.Huh SC.Kim SM. Tetrahedron Lett. 2001, 42: 6299 -
112e For an example of Michael reaction of indanones and methyl vinyl ketone, see:
Conn RSE.Lovell AV.Karady S.Weinstock LM. J. Org. Chem. 1986, 51: 4710 - 113
Poulsen TB.Bernardi L.Bell M.Jørgensen KA. Angew. Chem. Int. Ed. 2006, 45: 6551 - 114
Tozawa T.Nagao H.Yamane Y.Mukaiyama T. Chem. Asian J. 2007, 2: 123 -
115a
Donnoli MI.Scafato P.Nardiello M.Casarini D.Giorgio E.Rosini C. Tetrahedron 2004, 60: 4975 -
115b
Dere RT.Pal RR.Patil PS.Salunkhe MM. Tetrahedron Lett. 2003, 44: 5351 -
115c
Kim DY.Huh SC. Tetrahedron 2001, 57: 8933 -
115d
Perrard T.Plaquevent J.-C.Desmurs J.-R.Hébrault D. Org. Lett. 2000, 2: 2959 -
115e For an example of the use of an ephedrinium salt as catalyst, see:
Mirza-Aghayan M.Etemad-Moghadam G.Zaparucha A.Berlan J.Loupy A.Koenig M. Tetrahedron: Asymmetry 1995, 6: 2643 -
116a
Bakó P.Makó A.Keglevich G.Kubinyi M.Pái K. Tetrahedron: Asymmetry 2005, 16: 1861 -
116b
Töke L.Bakó P.Keserû GM.Albert M.Fenichel L. Tetrahedron 1998, 54: 213 -
116c
Brunet E.Poveda AM.Rabasco D.Oreja E.Font LM.Batra MS.Rodríguez-Ubis JC. Tetrahedron: Asymmetry 1994, 5: 935 - For revision, see:
-
117a
O’Donell MJ. Acc. Chem. Res. 2004, 37: 506 - See also:
-
117b
Ramachandran PV.Madhi S.Bland-Berry L.Reddy MVR.O’Donnell MJ. J. Am. Chem. Soc. 2005, 127: 13450 -
117c
Siebum AHG.Tsang RKF.van der Steen R.Raap J.Lugtenburg J. Eur. J. Org. Chem. 2004, 4391 -
117d
Akiyama T.Hara M.Fuchibe K.Sakamoto S.Yamaguchi K. Chem. Commun. 2003, 1734 -
117e
Corey EJ.Noe MC.Xu F. Tetrahedron Lett. 1998, 39: 5347 -
118a
Ishikawa T.Araki Y.Kumamoto T.Seki H.Fukuda K.Isobe T. Chem. Commun. 2001, 245: - See also
-
118b
Ma D.Cheng K. Tetrahedron: Asymmetry 1999, 10: 713 - 119
Terada M.Ube H.Yaguchi Y. J. Am. Chem. Soc. 2006, 128: 1454 -
120a
Allingham MT.Howard-Jones A.Murphy PJ.Thomas DA.Caulkett PWR. Tetrahedron Lett. 2003, 44: 8677 -
120b
Davis AP.Dempsey KJ. Tetrahedron: Asymmetry 1995, 6: 2829 - 121
Aroyan CE.Miller SJ. J. Am. Chem. Soc. 2007, 129: 256 - 122
Linton BR.Retuerzan MH.Aderman CM.Richardson EA.Brownell KR.Ashley CW.Evans CA.Miller SJ. Tetrahedron Lett. 2007, 48: 1993 - 123
Lattanzi A. Tetrahedron: Asymmetry 2006, 17: 837 - 124
Paras NA.MacMillan DWC. J. Am. Chem. Soc. 2001, 123: 4370 -
125a
Austin JF.MacMillan DWC. J. Am. Chem. Soc. 2002, 124: 1172 -
125b
Paras NA.MacMillan DWC. J. Am. Chem. Soc. 2002, 124: 7894 -
125c For a tandem enantioselective organocatalytic Friedel-Crafts alkylation-α-chlorination, see:
Huang Y.Walji AM.Larsen CH.MacMillan DWC. J. Am. Chem. Soc. 2005, 127: 15051 - 126
Gordillo R.Carter J.Houk KN. Adv. Synth. Catal. 2004, 346: 1175 -
127a
Bonini BF.Capito E.Comes-Franchini M.Fochi M.Ricci A.Zwanenburg B. Tetrahedron: Asymmetry 2006, 17: 3135 -
127b
Li D.-P.Guo Y.-C.Ding Y.Xiao W.-J. Chem. Commun. 2006, 799 -
127c
Breistein P.Karlsson S.Hedenström E. Tetrahedron: Asymmetry 2006, 17: 107 -
127d For a conjugate Friedel-Crafts alkylation of indoles with enones catalyzed by a cinchona alkaloid, see:
Bartoli G.Bosco M.Carlone A.Pesciaioli F.Sambri L.Melchiorre P. Org. Lett. 2007, 9: 1403 -
128a
Herrera RP.Sgarzani V.Bernardi L.Ricci A. Angew. Chem. Int. Ed. 2005, 44: 6576 -
128b For an example of a chiral camphorsulfonic acid catalyzed conjugate Friedel-Crafts alkylation of indoles with enones, see:
Zhou W.Xu L.-W.Li L.Yang L.Xia C.-G. Eur. J. Org. Chem. 2006, 5225 - 129 For a review, see:
Adolfsson H. Angew. Chem. Int. Ed. 2005, 44: 3340 -
130a
Ouellet SG.Tuttle JB.MacMillan DWC. J. Am. Chem. Soc. 2005, 127: 32 -
130b
Yang JW.Hechavarria-Fonseca MT.Vignola N.List B. Angew. Chem. Int. Ed. 2005, 44: 108 -
130c For an early report, see:
Yang JW.Hechavarria-Fonseca MT.List B. Angew. Chem. Int. Ed. 2004, 43: 6660 - 131
Tuttle JB.Ouellet SG.MacMillan DWC. J. Am. Chem. Soc. 2006, 128: 12662 - 132
Yang JW.Hechavarria-Fonseca MT.List B. J. Am. Chem. Soc. 2005, 127: 15036 - 133
Zhao G.-L.Córdova A. Tetrahedron Lett. 2006, 47: 7417 -
134a
Martin NJA.List B. J. Am. Chem. Soc. 2006, 128: 13368 -
134b
Mayer S.List B. Angew. Chem. Int. Ed. 2006, 45: 4193 - 135
Enders D.Lüttgen K.Narine AA. Synthesis 2007, 959 - 136
Marigo M.Schulte T.Franzén J.Jørgensen KA. J. Am. Chem. Soc. 2005, 127: 15710 - 137
Brandau S.Maerten E.Jørgensen KA. J. Am. Chem. Soc. 2006, 128: 14986 -
138a
Wang W.Li H.Wang J.Zu L. J. Am. Chem. Soc. 2006, 128: 10354 -
138b
Rios R.Sundén H.Ibrahem I.Zhao G.-L.Eriksson L.Córdova A. Tetrahedron Lett. 2006, 47: 8547 - 139
Rios R.Sundén H.Ibrahem I.Zhao G.-L.Córdova A. Tetrahedron Lett. 2006, 47: 8679 - 140
Li H.Zu L.Xie H.Wang J.Jiang W.Wang W. Org. Lett. 2007, 9: 1833 - 141
Li B.-J.Jiang J.Liu M.Chen Y.-C.Ding L.-S.Wu Y. Synlett 2005, 603 - 142
Zu L.Wang J.Li H.Xie H.Jiang W.Wang W. J. Am. Chem. Soc. 2007, 129: 1036 - 143
Li H.Wang J.Zu L.-S.Wang W. Tetrahedron Lett. 2006, 47: 2585 -
144a
Li H.Zu L.Wang J.Wang W. Tetrahedron Lett. 2006, 47: 3145 -
144b For an earlier cinchone-catalyzed version of this reaction, see:
Gawronski J.Gawronska K.Wynberg H. J. Chem. Soc., Chem. Commun. 1981, 307 - 145
Kobayashi N.Iwai K. J. Org. Chem. 1981, 46: 1823 - 146
Helder R.Arends R.Bolt W.Hiemstra H.Wynberg H. Tetrahedron Lett. 1977, 12: 2181 -
147a
Kumar A.Salunkhe RV.Rane RA.Dike SY. J. Chem. Soc., Chem. Commun. 1991, 485 -
147b
Sera A.Takagi K.Katayama H.Yamada H.Matsumoto K. J. Org. Chem. 1988, 53: 1157 -
147c
Ahuja RR.Natu AA.Gogte VN. Tetrahedron Lett. 1980, 21: 4743 -
147d
Danelli T.Annunziata R.Benaglia M.Cinquini M.Cozzi F.Tocco G. Tetrahedron: Asymmetry 2003, 14: 461 -
147e Mukaiyama has employed a simple chiral amino alcohol that mimicks the structure of cinchone alkaloids:
Mukaiyama T. Tetrahedron 1981, 37: 4111 -
148a
Skarżewski J.Zielińska-Bajet M.Turowska-Tyr I. Tetrahedron: Asymmetry 2001, 12: 1392 -
148b
Zielińska-Bajet M.Kowalczyk R.Skarżewski J. Tetrahedron 2005, 61: 5235 - 149
McDaid P.Chen Y.Deng L. Angew. Chem. Int. Ed. 2002, 41: 338 - Reviews:
-
150a
Vicario JL.Badía L.Carrillo L.Etxebarria J.Reyes E.Ruiz N. Org. Prep. Proced. Int. 2005, 37: 513 -
150b
Xu L.-W.Xia C.-G. Eur. J. Org. Chem. 2005, 633 - 151 For a review on peptide-based organocatalysts, see:
Miller SJ. Acc. Chem. Res. 2004, 37: 601 -
152a
Horstmann TE.Guerin DJ.Miller SJ. Angew. Chem. Int. Ed. 2000, 39: 3365 -
152b
Guerin DJ.Miller SJ. J. Am. Chem. Soc. 2002, 124: 2134 -
153a
Chen YK.Yoshida M.MacMillan DWC. J. Am. Chem. Soc. 2006, 128: 9328 -
153b For a later report using the same nucleophile and catalyst 8a, see:
Vesely J.Ibrahem I.Rios R.Zhao G.-L.Xu Y.Córdova A. Tetrahedron Lett. 2007, 48: 2193 -
153c For an example of amine-catalyzed conjugate addition of hydrazoic acid to nitroalkenes, see:
Nielsen M.Zhuang W.Jorgensen K. A. Tetrahedron 2007, 63: 5849 - 154
Edwards JO.Pearson RG. J. Am. Chem. Soc. 1962, 84: 16 - 155
Ibrahem I.Rios R.Vesely J.Zhao G.-L.Córdova A. Chem. Commun. 2007, 849 - 156
Vesely J.Ibrahem I.Zhao G.-L.Rios R.Córdova A. Angew. Chem. Int. Ed. 2007, 46: 778 -
157a
Li H.Wang J.Xie H.Zu L.Jiang W.Duesler EN.Wang W. Org. Lett. 2007, 9: 965 -
157b
Sundén H.Rios R.Ibrahem I.Zhao G.-L.Eriksson L.Córdova A. Adv. Synth. Catal. 2007, 349: 827 - 158
Dinér P.Nielsen M.Marigo M.Jørgensen KA. Angew. Chem. Int. Ed. 2007, 46: 1983 - 159
Uria U.Vicario JL.Badía D.Carrillo L. Chem. Commun. 2007, 2509 - 160
Wang J.Li H.Zu L.Wang W. Org. Lett. 2006, 8: 1391 - 161
Perdicchia D.Jørgensen KA. J. Org. Chem. 2007, 72: 3565 - 162
Sohtome Y.Tanatani A.Hashimoto Y.Nagasawa K. Chem. Pharm. Bull. 2004, 52: 477 - 163
Tanaka T.Kumamoto T.Ishikawa Y. Tetrahedron: Asymmetry 2000, 11: 4633 - 164
Merschaert A.Delbeke P.Daloze D.Dive G. Tetrahedron Lett. 2004, 45: 4697 - 165
Biddle MM.Lin M.Scheidt KA. J. Am. Chem. Soc. 2007, 129: 3830 -
166a
Sundén H.Ibrahem I.Zhao G.-L.Eriksson L.Córdova A. Chem. Eur. J. 2007, 13: 574 -
166b For an earlier attempt, see:
Govender T.Hojabri L.Moghaddam FM.Arvidsson PI. Tetrahedron: Asymmetry 2006, 17: 1763 - 167
Bertelsen S.Dinér P.Johansen RL.Jørgensen KA. J. Am. Chem. Soc. 2007, 129: 1536 - Catalyst 11c:
-
168a
Lattanzi A. Adv. Synth. Catal. 2006, 348: 339 - Catalyst 8d:
-
168b
Marigo M.Franzén J.Poulsen TB.Zhuang W.Jørgensen KA. J. Am. Chem. Soc. 2005, 127: 6964 - Catalyst 8a:
-
168c
Sundén H.Ibrahem I.Córdova A. Tetrahedron Lett. 2006, 47: 99 -
168d
Zhao G.-L.Dziedzic P.Ibrahem I.Córdova A. Synlett 2006, 3521 - Catalyst 52:
-
168e
Li Y.Liu X.Yang Y.Zhao G. J. Org. Chem. 2007, 72: 288 - Catalyst ent -17c:
-
168f
Lee S.MacMillan DWC. Tetrahedron 2006, 62: 11413 -
169a
Lygo B.Wainwright PG. Tetrahedron 1999, 55: 6289 -
169b
Corey EJ.Zhang F.-Y. Org. Lett. 1999, 1: 1287 - 170 For a general review, see:
Enders D.Saint-Dizier A.Lannou M.-I.Lenzen A. Eur. J. Org. Chem. 2006, 29 - 171
Bartoli G.Bosco M.Carlone A.Locatelli M.Mazzanti A.Sambri L.Melchiorre P. Chem. Commun. 2007, 722 -
172a
Carlone A.Bartoli G.Bosco M.Sambri L.Melchiorre P. Angew. Chem. Int. Ed. 2007, 46: 4504 -
172b
Ibrahem I.Rios R.Vesely J.Hammar P.Eriksson L.Himo F.Córdova A. Angew. Chem. Int. Ed. 2007, 46: 4507 -
172c For another very recently appeared quinine-catalyzed addition of diphenyl phosphite to nitroalkenes, see:
Wang J.Heikkinen L. D.Li H.Zu L.Jiang W.Xie H.Wang W. Adv. Synth. Catal. 2007, 349: 1052 - 173
Kunz RK.MacMillan DWC. J. Am. Chem. Soc. 2005, 127: 3240 - 174 Review:
Marion N.Díez-González S.Nolan SP. Angew. Chem. Int. Ed. 2007, 46: 2988 - 175
Phillips EM.Wadamoto M.Chan A.Scheidt KA. Angew. Chem. Int. Ed. 2007, 46: 3107 - 176
Enders D.Balensiefer T. Acc. Chem. Res. 2004, 37: 534 - 177
Enders D.Breuer K.Runsik J. Helv. Chim. Acta 1996, 79: 1899 -
178a
Kerr MS.Read de Alaniz J.Rovis T. J. Am. Chem. Soc. 2002, 124: 10298 -
178b
Kerr MS.Rovis T. Synlett 2003, 1934 -
178c For the application of a modified catalyst 55 in the same reaction generating a quaternary stereocenter, see:
Kerr MS.Rovis T. J. Am. Chem. Soc. 2004, 126: 8876 - 179
Mennen SM.Blank JT.Tran-Dubé MB.Imbriglio JE.Miller SJ. Chem. Commun. 2005, 195 - 180
Mattson AE.Zuhl AM.Reynolds TE.Scheidt KA. J. Am. Chem. Soc. 2006, 128: 4932 - 181
Enders D.Bonten MH.Raabe G. Synlett 2007, 885 - 182 Recent review:
de Figueiredo RM.Christmann M. Eur. J. Org. Chem. 2007, 2575