Diarylprolinol Silyl Ether Salts as New, Efficient, Water-Soluble, and Recyclable Organocatalysts for the Asymmetric Michael Addition on Water

被引:195
作者
Zheng, Zilong [1 ]
Perkins, Benjamin L. [1 ]
Ni, Bukuo [1 ]
机构
[1] Texas A&M Univ, Dept Chem, Commerce, TX 75429 USA
基金
美国国家科学基金会;
关键词
CONJUGATE ADDITION; ACID CATALYSTS; ALDEHYDES; KETONES; NITROOLEFINS; NITROALKENES;
D O I
10.1021/ja9093583
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel strategy for the catalytic asymmetric Michael addition of aldehydes to nitroolefins on water has been developed and provided the Michael adducts in excellent diastereo- and enantioselectivities. A notable feature of these organocatalysts is that they can be recycled for more than six times without a significant loss of catalytic activity and stereochemical control. In addition, the synthetic procedure presented is simple, practical, and environmentally benign.
引用
收藏
页码:50 / +
页数:4
相关论文
共 30 条
[1]   Organocatalytic asymmetric conjugate additions [J].
Almasi, Diana ;
Alonso, Diego A. ;
Najera, Carmen .
TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365
[2]   Highly enantioselective Michael additions in water catalyzed by a PS-Supported pyrrolidine [J].
Alza, Esther ;
Cambeiro, Xacobe C. ;
Jimeno, Ciril ;
Pericas, Miquel A. .
ORGANIC LETTERS, 2007, 9 (19) :3717-3720
[3]   Chiral piperazines as efficient catalysts for the asymmetric Michael addition of aldehydes to nitroalkenes [J].
Barros, Maria Teresa ;
Phillips, Ana Maria Faisca .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (01) :178-185
[4]   Enantioselective Organocatalytic Conjugate Addition of Aldehydes to Nitrodienes [J].
Belot, Sebastien ;
Massaro, Assunta ;
Tenti, Alice ;
Mordini, Alessandro ;
Alexakis, Alexandre .
ORGANIC LETTERS, 2008, 10 (20) :4557-4560
[5]  
Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[6]   Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].
Betancort, JM ;
Barbas, CF .
ORGANIC LETTERS, 2001, 3 (23) :3737-3740
[7]   Enamine-based aldol organocatalysis in water: Are they really "all wet"? [J].
Brogan, Andrew P. ;
Dickerson, Tobin J. ;
Janda, Kim D. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (48) :8100-8102
[8]   Enantioselective organocatalytic conjugate addition of N heterocycles to α,β-unsaturated aldehydes [J].
Diner, Peter ;
Nielsen, Martin ;
Marigo, Mauro ;
Jorgensen, Karl Anker .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (12) :1983-1987
[9]   Enantioselective nitro-Michael reactions catalyzed by short peptides on water [J].
Freund, Matthias ;
Schenker, Sebastian ;
Tsogoeva, Svetlana B. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (20) :4279-4284
[10]   Enantioselective direct aldol reaction "on water" promoted by chiral organic catalysts [J].
Guizzetti, Stefania ;
Benaglia, Maurizio ;
Raimondi, Laura ;
Celentano, Giuseppe .
ORGANIC LETTERS, 2007, 9 (07) :1247-1250