Enantioselective Intermolecular Crossed-Conjugate Additions between Nitroalkenes and α,β-Enals through a Dual Activation Strategy

被引:68
作者
Zhong, Cheng [1 ]
Chen, Yunfeng [1 ]
Petersen, Jeffrey L. [1 ]
Akhmedov, Novruz G. [1 ]
Shi, Xiaodong [1 ]
机构
[1] W Virginia Univ, C Eugene Bennett Dept Chem, Morgantown, WV 26506 USA
关键词
asymmetric catalysis; enantioselectivity; Lewis bases; pyrrolidines; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; ALDEHYDES; ORGANOCATALYSIS; STEREOCENTERS; CATALYSIS; PROLINE;
D O I
10.1002/anie.200805558
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Double the fun: The title reaction was developed by using a Lewis base/iminium activation strategy (see scheme). The reaction proceeded with excellent yields and ee values, and the products were additionally transformed into a single enantiomer of a substituted pyrrolidine with excellent retention of configuration. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1279 / 1282
页数:4
相关论文
共 33 条
[1]   The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins [J].
Andrey, O ;
Alexakis, A ;
Tomassini, A ;
Bernardinelli, G .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1147-1168
[2]  
[Anonymous], 2008, ANGEW CHEM
[3]  
[Anonymous], 2006, ANGEW CHEM
[4]   The Baylis-Hillman reaction: a novel source of attraction, opportunities, and challenges in synthetic chemistry [J].
Basavaiah, Deevi ;
Rao, Kalapala Venkateswara ;
Reddy, Raju Jannapu .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) :1581-1588
[5]  
Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[6]   Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes:: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones [J].
Brandau, Sven ;
Landa, Aitor ;
Franzen, Johan ;
Marigo, Mauro ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4305-4309
[7]  
Carlone A., 2007, Angew. Chem, V119, P1119
[8]   A new approach for an organocatalytic multicomponent domino asymmetric reaction [J].
Carlone, Armando ;
Cabrera, Silvia ;
Marigo, Mauro ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (07) :1101-1104
[9]   Enantioselective [3+2]-cycloadditions catalyzed by a protected, multifunctional phosphine-containing α-amino acid [J].
Cowen, Bryan J. ;
Miller, Scott J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :10988-+
[10]   Alcohol-assisted phosphine catalysis: One-step syntheses of dihydropyrones from aldehydes and allenoates [J].
Creech, Gardner S. ;
Kwon, Ohyun .
ORGANIC LETTERS, 2008, 10 (03) :429-432