Ionic Liquid-Supported (ILS) (S)-Pyrrolidine Sulfonamide for Asymmetric Michael Addition Reactions of Aldehydes with Nitroolefins

被引：0

作者：

Omar, Emmy M. ^{[2
]}

Dhungana, Kritanjali ^{[1
]}

Headley, Allan D. ^{[1
]}

Rahman, Mohd Basyaruddin Abdul ^{[2
]}

机构：

[1] Texas A&M Univ, Dept Chem, Commerce, TX 75429 USA

[2] Univ Putra Malaysia, Dept Chem, Fac Sci, Upm Serdang 43400, Selangor, Malaysia

来源：

LETTERS IN ORGANIC CHEMISTRY | 2011年 / 8卷 / 03期

关键词：

Aldehydes; asymmetric catalysis; ionic liquid; michael addition; nitroolefins; EFFICIENT ORGANOCATALYSTS; CONJUGATE ADDITION; KETONES; CATALYSTS; NITROALKENES; STRATEGY; PROLINE;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A class of ionic liquid supported (ILS) (S)-pyrrolidine sulfonamide organocatalyst (1c), which was developed earlier in our lab, has been applied to a wider range of Michael addition reaction, involving various aryl-substituted nitroolefins and a series of aldehydes. Catalyst 1c catalyzes Michael additions in which only 2 equivalents of aldehydes to each equivalent of nitroolefin are required. With 10 mol% of ILS catalyst 1c loading, moderate to excellent yields (51-98%) with moderate enantioselectivities (28-83% ee) and high diastereoselectivities (syn/anti ratio up to 97/3) were obtained. Moreover, the catalyst 1c could be easily recycled and reused for at least 5 times with slightly reduced activities.

引用

页码：170 / 175

页数：6

共 50 条

[31] Ono N., 2001, The Nitro Group in Organic Synthesis
[32] Highly efficient asymmetric Michael addition of aldehydes to nitroalkenes catalyzed by a simple trans-4-hydroxyprolylamide
Palomo, Claudio
Vera, Silvia
Mielgo, Antonia
Gomez-Bengoa, Enrique
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (36) : 5984 - 5987
[33] Simple diamine- and triamine-protonic acid catalysts for the enantioselective Michael addition of cyclic ketones to nitroalkenes
Pansare, Sunil V.
Pandya, Keyur
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) : 9624 - 9625
[34] Rosini G., 1991, COMPREHENSIVE ORGANI, V2, P321, DOI DOI 10.1016/B978-0-08-052349-1.00032-9
[35] Amino acid catalyzed direct asymmetric aldol reactions: A bioorganic approach to catalytic asymmetric carbon-carbon bond-forming reactions
Sakthivel, K
Notz, W
Bui, T
Barbas, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) : 5260 - 5267
[36] Asymmetric organocatalysis
Seayad, J
List, B
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (05) : 719 - 724
[37] Chiral amines as organocatalysts for asymmetric conjugate addition to nitroolefins and vinyl sulfones via enamine activation
Sulzer-Mosse, Sarah
Alexakis, Alexandre
[J]. CHEMICAL COMMUNICATIONS, 2007, (30) : 3123 - 3135
[38] Highly enantioselective (S)-homoproline-catalyzed Michael addition reactions of ketones to β-nitrostyrenes
Terakado, D
Takano, M
Oriyama, T
[J]. CHEMISTRY LETTERS, 2005, 34 (07) : 962 - 963
[39] Are Ionic Liquids Suitable Media for Organocatalytic Reactions?
Toma, Stefan
Meciarova, Maria
Sebesta, Radovan
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (03) : 321 - 327
[40] Recent advances in asymmetric organocatalytic 1,4-conjugate additions
Tsogoeva, Svetlana B.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (11) : 1701 - 1716

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