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
Download PDF
Synthesis 2007(16): 2571-2575
DOI: 10.1055/s-2007-983795
DOI: 10.1055/s-2007-983795
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New YorkChiral-Thiourea-Catalyzed Direct Mannich Reaction
Further Information
Received
1 January 2007
Publication Date:
12 July 2007 (online)
Publication History
Publication Date:
12 July 2007 (online)
Abstract
In the presence of a chiral thiourea as a bifunctional organocatalyst, Mannich reaction of N-Boc-imine with prochiral 1,3-dicarbonyl compounds proceeded with excellent enantio- and diastereoselectivities.
Key words
organocatalyst - thiourea - enantioselective - Mannich reaction - imine
- For recent reviews on organocatalyst chemistry, see:
- 1a
Dalko PI.Moisan L. Angew. Chem. Int. Ed. 2001, 40: 3726 - 1b
Pihko PM. Angew. Chem. Int. Ed. 2004, 43: 2062 - 1c
Dalko PI.Moisan L. Angew. Chem. Int. Ed. 2004, 43: 5138 - 1d Special Issue on Asymmetric Organocatalysis: Acc. Chem. Res. 2004, 37: 487-631
- 1e
Bolm C.Rantanen T.Schiffers I.Zani L. Angew. Chem. Int. Ed. 2005, 44: 1758 - 1f Special Issue on Organocatalysis: Adv. Synth. Catal. 2004, 346: 1007-1249
- 1g
Seayad J.List B. Org. Biomol. Chem. 2005, 3: 719 - 1h
Takemoto Y. Org. Biomol. Chem. 2005, 3: 4299 - 1i
Taylor MS.Jacobsen EN. Angew. Chem. Int. Ed. 2006, 45: 1520 - The potential of ureas and thioureas to serve as organocatalysts has recently begun to be explored by several groups, see:
- 2a
Curran DP.Kuo LH. J. Org. Chem. 1994, 59: 3259 - 2b
Curran DP.Kuo LH. Tetrahedron Lett. 1995, 36: 6647 - 2c
Wilcox CS.Kim E.Romano D.Kuo LH.Curran DP. Tetrahedron 1995, 51: 621 - 2d
Sigman MS.Jacobsen EN. J. Am. Chem. Soc. 1998, 120: 4901 - 2e
Vachal P.Jacobsen EN. Org. Lett. 2000, 2: 867 - 2f
Sigman MS.Vachal P.Jacobsen EN. Angew. Chem. Int. Ed. 2000, 39: 1279 - 2g
Vachal P.Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 10012 - 2h
Wenzel AG.Jacobsen EN. J. Am. Chem. Soc. 2002, 124: 12964 - 2i
Joly GD.Jacobsen EN. J. Am. Chem. Soc. 2004, 126: 4102 - 2j
Taylor MS.Jacobsen EN. J. Am. Chem. Soc. 2004, 126: 10558 - 2k
Schreiner PR.Wittkopp A. Org. Lett. 2002, 4: 217 - 2l
Wittkopp A.Schreiner PR. Chem. Eur. J. 2003, 9: 407 - For examples of urea-catalyzed reactions, see:
- 3a
Sohtome Y.Tanatani A.Hashimoto Y.Nagasawa K. Chem. Pharm. Bull. 2004, 52: 477 - 3b
Maher DJ.Connon SJ. Tetrahedron Lett. 2004, 45: 1301 - 3c
Sohtome Y.Tanatani A.Hashimoto Y.Nagasawa K. Tetrahedron Lett. 2004, 45: 5589 - 3d
Yoon TP.Jacobsen EN. Angew. Chem. Int. Ed. 2005, 44: 466 - 3e
Taylor MS.Tokunaga N.Jacobsen EN. Angew. Chem. Int. Ed. 2005, 44: 6700 - 3f
Fuerst DE.Jacobsen EN. J. Am. Chem. Soc. 2005, 127: 8964 - 3g
Raheem IT.Jacobsen EN. Adv. Synth. Catal. 2005, 347: 1701 - 3h
Berkessel A.Cleemann F.Mukherjee S.Müller TN. Angew. Chem. Int. Ed. 2005, 44: 807 - 3i
Berkessel A.Mukherjee S.Cleemann F.Müller TN. Chem. Commun. 2005, 1898 - 3j
Li B.-J.Jiang L.Liu M.Chen Y.-C.Ding L.-S.Wu Y. Synlett 2005, 603 - 3k
Vakulya B.Varga A.Csampai A.Soos T. Org. Lett. 2005, 7: 1967 - 3l
McCooey SH.Connon SJ. Angew. Chem. Int. Ed. 2005, 44: 6367 - 3m
Herrera RP.Sgarzani V.Bernardi L.Ricci A. Angew. Chem. Int. Ed. 2005, 44: 6576 - 3n
Wang J.Li H.Yu X.Zu L.Wang W. Org. Lett. 2005, 7: 4293 - 3o
Wang J.Li H.Duan W.Zu L.Wang W. Org. Lett. 2005, 7: 4713 - 3p
Berkessel A.Cleemann F.Mukherjee S. Angew. Chem. Int. Ed. 2005, 44: 7466 - 3q
Ye J.Dixon DJ.Hynes PS. Chem. Commun. 2005, 4481 - 3r
Tsogoeva SB.Yalalov DA.Hateley MJ.Weckbecker C.Huthmacher K. Eur. J. Org. Chem. 2005, 4995 - 3s
Sohtome Y.Hashimoto Y.Nagasawa K. Adv. Synth. Catal. 2005, 347: 1643 - 3t
Marcelli T.van der Haas RNS.van Maarseveen JH.Hiemstra H. Angew. Chem. Int. Ed. 2006, 45: 929 - 3u
Dixon DJ.Richardson RD. Synlett 2006, 81 - For our studies on urea-catalyzed reactions, see:
- 4a
Okino T.Hoashi Y.Takemoto Y. Tetrahedron Lett. 2003, 44: 2817 - 4b
Okino T.Hoashi Y.Takemoto Y. J. Am. Chem. Soc. 2003, 125: 12672 - 4c
Okino T.Nakamura S.Furukawa T.Takemoto Y. Org. Lett. 2004, 6: 625 - 4d
Hoashi Y.Okino T.Takemoto Y. Angew. Chem. Int. Ed. 2005, 44: 4032 - 4e
Hoashi Y.Yabuta T.Takemoto Y. Tetrahedron Lett. 2004, 45: 9185 - 4f
Okino T.Hoashi Y.Furukawa T.Xu X.Takemoto Y. J. Am. Chem. Soc. 2005, 127: 119 - 4g
Hoashi Y.Yabuta T.Yuan P.Miyabe H.Takemoto Y. Tetrahedron 2006, 62: 365 - 4h
Xu X.Furukawa T.Okino T.Miyabe H.Takemoto Y. Chem. Eur. J. 2006, 12: 466 - 4i
Xu X.Yabuta T.Yuan P.Takemoto Y. Synlett 2006, 137 - 4j
Inokuma T.Hoashi Y.Takemoto Y. J. Am. Chem. Soc. 2006, 128: 9413 - 4k
Miyabe H.Tuchida S.Yamauchi M.Takemoto Y. Synthesis 2006, 3295 - 5 For a review of catalytic asymmetric direct Mannich reactions, see:
Córdova A. Acc. Chem. Res. 2004, 37: 102 - For some recent examples of direct asymmetric Mannich reactions, see:
- 6a
Ting A.Lou S.Schaus SE. Org. Lett. 2006, 8: 2003 - 6b
Lou S.Taoka BM.Ting A.Schaus SE. J. Am. Chem. Soc. 2005, 127: 11256 - 6c
Hamashima Y.Sasamoto N.Hotta D.Somei H.Umebayashi N.Sodeoka M. Angew. Chem. Int. Ed. 2005, 44: 1525 - 6d
Uraguchi D.Terada M. J. Am. Chem. Soc. 2004, 126: 5356 - 6e
Matsunaga S.Yoshida T.Morimoto H.Kumagai N.Shibasaki M. J. Am. Chem. Soc. 2004, 126: 8777 - 6f
Zhuang W.Saaby S.Jørgensen KA. Angew. Chem. Int. Ed. 2004, 43: 4476 - 6g
Cobb AJA.Shaw DM.Ley SV. Synlett 2004, 558 - 6h
Córdova A. Chem. Eur. J. 2004, 10: 1987 - 7a
Song J.Wang Y.Deng L. J. Am. Chem. Soc. 2006, 128: 6048 - 7b
Tillman AL.Ye J.Dixon DJ. Chem. Commun. 2006, 1191