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 2004(18): 2943-2958
DOI: 10.1055/s-2004-834932
DOI: 10.1055/s-2004-834932
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Recent Advances in the Asymmetric Hydrosilylation of Ketones, Imines and Electrophilic Double Bonds
Further Information
Received
14 July 2004
Publication Date:
24 November 2004 (online)
Publication History
Publication Date:
24 November 2004 (online)
Abstract
This literature review focuses on the recent advances in the asymmetric hydrosilylation of ketones and imines. New catalyst systems based on various transition metals, such as rhodium, titanium, zinc, copper and tin, combined with classical or new ligand structures, are presented. These systems lead to very effective and selective protocols for the reduction of prochiral ketones, imines and electrophilic double bonds.
1 Introduction
2 Rhodium-Based Catalysts
3 Titanium-Based Catalysts
3.1 Hydrosilylation of Ketones
3.2 Hydrosilylation of Imines
4 Zinc-Based Catalysts
5 Copper-Based catalysts
5.1 Asymmetric Hydrosilylation of Electrophilic Double Bonds
5.2 Asymmetric Hydrosilylation of Ketones and Imines
6 Conclusions
Key words
asymmetric catalysis - asymmetric hydrosilylation - chiral ligands - rhodium - titanium - zinc - conjugate addition - reduction
- 1
Langlois N.Dang TP.Kagan HB. Tetrahedron Lett. 1973, 49: 4865 - 2
Dumont W.Poulin J.-C.Dang TP.Kagan HB. J. Am. Chem. Soc. 1973, 95: 8295 - 3
Nishiyama H. Hydrosilylation of carbonyl and imino groups, In Comprehensive Asymmetric CatalysisJacobsen EN.Pfaltz A.Yamamoto H. Springer-Verlag; Berlin: 1999. Chap. 63. - 4
Noyori R. Asymmetric catalysis in organic synthesis Wiley-VCH; New York: 1994. - 5
Itsuno S. Enantioselective reduction of ketones: Hydrosilylation, In Organic Reactions Vol. 52:Paquette LA. Wiley-VCH; Weinheim: 1998. p.440 - 6
Carpentier J.-F.Bette V. Curr. Org. Chem. 2002, 6: 913 - 7
Kuwano R.Sawamura M.Shirai J.Takahashi M.Ito Y. Tetrahedron Lett. 1995, 36: 5239 - 8
Sawamura M.Kuwano R.Ito Y. Angew. Chem., Int. Ed. Engl. 1994, 33: 111 - 9
Sawamura M.Kuwano R.Shirai J.Ito Y. Synlett 1995, 347 - 10
Kuwano R.Uemura T.Saitoh M.Ito Y. Tetrahedron Lett. 1999, 40: 1327 - 11
Kuwano R.Sawamura M.Shirai J.Takahashi M.Ito Y. Bull. Chem. Soc. Jpn. 2000, 73: 485 - 12
Brunner H.Becker R.Riepi G. Organometallics 1984, 3: 1354 - 13
Nishiyama H.Kondo M.Nakamura T.Itoh K. Organometallics 1991, 10: 500 - 14
Nishiyama H.Yamagushi S.Kondo M.Itoh K. J. Org. Chem. 1992, 57: 4306 - 15
Langer T.Janssen J.Helmchen G. Tetrahedron: Asymmetry 1996, 7: 1599 - 16
Newman LM.Williams JMJ.McCague R.Potter GA. Tetrahedron: Asymmetry 1996, 7: 1597 - 17
Yasuike S.Okajima S.Yamaguchi K.Seki H.Kurita J. Tetrahedron: Asymmetry 2000, 11: 4043 - 18
Heldmann DK.Seebach D. Helv. Chim. Acta 1999, 82: 1096 - 19
Hayashi T.Hayashi C.Uozumi Y. Tetrahedron: Asymmetry 1995, 6: 2503 - 20
Karamé I.Tommasino ML.Lemaire M. J. Mol. Catal. A: Chem. 2003, 196: 137 - 21
Gomez M.Jansat S.Muller G.Bonnet MC.Breuzard JAJ.Lemaire M. J. Organomet. Chem. 2002, 659: 186 - 22
Gavrilov KN.Bondarev OG.Lebedev RV.Polosukhin AI.Shyryaev A.Lyubimov SE.Petrovskii PV.Moiseev SK.Kalinin VN.Ikonnikov NS.Davankov VA.Korostylev AV. J. Organomet. Chem. 2002, 655: 204 - 23
Graf v. Keyserlingk N.Martens J. Tetrahedron: Asymmetry 2001, 12: 2213 - 24
Suarez A.Pizzano A.Fernandez I.Khiar N. Tetrahedron: Asymmetry 2001, 12: 633 - 25
Saitoh A.Uda T.Morimoto T. Tetrahedron: Asymmetry 1999, 10: 4501 - 26
Tsuruta H.Imamoto T. Tetrahedron: Asymmetry 1999, 10: 877 - 27
Tao B.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 3892 - 28
Yao S.Meng J.-C.Siuzdak G.Finn MG. J. Org. Chem. 2003, 68: 2540 - 29
Evans DA.Michael FE.Tedrow JS.Campos KR. J. Am. Chem. Soc. 2003, 125: 3534 - 30
Takei I.Nishibayashi Y.Ishii Y.Mizobe Y.Uemura S.Hidai M. Chem. Commun. 2001, 2360 - 31
Nishibayashi Y.Segawa K.Ohe K.Uemura S. Organometallics 1995, 14: 5486 - 32
Enders D.Gielen H. J. Organomet. Chem. 2001, 617-618: 70 - 33
Gade LH.César V.Bellemin-Laponnaz S. Angew. Chem. Int. Ed. 2004, 43: 1014 - 34
Duan W.-L.Shi M.Rong G.-B. Chem. Commun. 2003, 2916 - 35
Carter MB.Schiott B.Gutiérrez A.Buchwald SL. J. Am. Chem. Soc. 1994, 116: 11667 - 36
Halterman RL.Ramsey TM.Chen Z. J. Org. Chem. 1994, 59: 2642 - 37
Harrod JF.Xin S. Can. J. Chem. 1995, 73: 999 - 38
Lawrence NJ.Drew MDM.Bushell SM. J. Chem. Soc., Perkin Trans. 1 1999, 3381 - 39
Rahimian K.Harrod JF. Inorg. Chim. Acta 1998, 270: 330 - 40
Yun J.Buchwald SL. J. Am. Chem. Soc. 1999, 121: 5640 - 41
Beagley P.Davies PJ.Blacker AJ.White C. Organometallics 2002, 21: 5852 - 42
Imma H.Mori M.Nakai T. Synlett 1996, 1229 - 43
Bandini M.Bernardi F.Bottoni A.Cozzi PG.Miscione GP.Umani-Ronchi A. Eur. J. Org. Chem. 2003, 2972 - 44
Bandini M.Cozzi PG.Negro L.Umani-Ronchi A. Chem. Commun. 1999, 39 - 45
Verdaguer X.Lange UEW.Reding MT.Buchwald SL. J. Am. Chem. Soc. 1996, 118: 6784 - 46
Verdaguer X.Lange UEW.Buchwald SL. Angew. Chem. Int. Ed. 1998, 37: 81103 - 47
Hansen MC.Buchwald SL. Org. Lett. 2000, 2: 713 - 48
Yun J.Buchwald SL. J. Org. Chem. 2000, 65: 767 - 49
Reding MT.Buchwald SL. J. Org. Chem. 1998, 63: 6344 - 50
Hansen MC.Buchwald SL. Tetrahedron Lett. 1999, 40: 2033 - 51
Mimoun H. inventors; WO 96/12694. ; Chem. Abstr. 1996, 125, 114173 - 52
Mimoun H. J. Org. Chem. 1999, 64: 2582 - 53
Mimoun H. inventors; 23WO 99/12877. ; Chem. Abstr. 1999, 130, 237357 - 54
Mimoun H.de Saint Laumer JY.Giannini L.Scopelliti R.Floriani C. J. Am. Chem. Soc. 1999, 121: 6158 - 55
Mastranzo VM.Quintero L.de Parodi CA.Juaristi E.Walsh PJ. Tetrahedron 2004, 60: 1781 - 56
Bette V.Mortreux A.Svoia D.Carpentier J.-F. Tetrahedron 2004, 60: 2837 - 57
Lipshutz BH. Copper(I)-mediated 1,2- and 1,4-reductions, In Modern Organocopper ChemistryKrause N. Wiley-VCH; Weinheim: 2002. p.167 - 58
Mahoney WS.Stryker JM. J. Am. Chem. Soc. 1989, 111: 8818 - 59
Appella DH.Moritani Y.Shintani R.Ferreira EM.Buchwald SL. J. Am. Chem. Soc. 1999, 121: 9473 - 60
Hughes G.Kimura M.Buchwald SL. J. Am. Chem. Soc. 2003, 125: 11253 - 61
Moritani Y.Appella DH.Jurkauskas V.Buchwald SL. J. Am. Chem. Soc. 2000, 122: 6797 - 62
Yun J.Buchwald SL. Org. Lett. 2001, 3: 1129 - 63
Jurkauskas V.Buchwald SL. J. Am. Chem. Soc. 2002, 124: 2892 - 64
Lipshutz BH.Lower A.Noson K. Org. Lett. 2002, 4: 4045 - 65
Lipshutz BH.Servesko JM.Peterson TB.Papa P.Lover AA. Org. Lett. 2004, 6: 1273 - 66
Lipshutz BH.Servesko JM. Angew. Chem. Int. Ed. 2003, 42: 4789 - 67
Czekelius C.Carreira EM. Angew. Chem. Int. Ed. 2003, 42: 4793 - 68
Lipshutz BH.Noson K.Chrisman W. J. Am. Chem. Soc. 2001, 123: 12917 - 69
Sirol S.Courmarcel J.Mostefaï N.Riant O. Org. Lett. 2001, 3: 4111 - 70
Courmarcel J.Mostefaï N.Sirol S.Chopin S.Riant O. Isr. J. Chem. 2002, 41: 231 - 71
Lipshutz BH.Caires CC.Kuipers P.Chrisman W. Org. Lett. 2003, 5: 3085 - 72
Lipshutz BH.Shimizu H. Angew. Chem. Int. Ed. 2004, 43: 2228 - 73
Kryzyzanowska B.Stec WJ. Synthesis 1978, 521 - 74
Spindler F.Blaser HU. Adv. Synth. Catal. 2001, 343: 68 - 75
Sugi KD.Nagata T.Yamada T.Mukaiyama T. Chem. Lett. 1997, 493 - 76
Kryzyzanowska B.Stec WJ. Synthesis 1982, 270 - 77
Baser HU.Spindler F.Studer M. Appl. Catal., A 2001, 221: 119 - 78
Kaur H.Zinn KF.Stevens ED.Nolan SP. Organometallics 2004, 23: 1157 - 79
Jurkauskas V.Sadaghi JP.Buchwald SL. Org. Lett. 2003, 5: 2417 - 80
Lawrence NJ.Bushell SM. Tetrahedron 2000, 41: 4507 - 81
Ireland T.Fontanet F.Tchao G.-G. Tetrahedron Lett. 2004, 45: 4383