In Situ Enamine Activation in Aqueous Salt Solutions: Highly Efficient Asymmetric Organocatalytic Diels-Alder Reaction of Cyclohexenones with Nitroolefins

被引：96

作者：

Xu, Dan-Qian ^{[1
]}

Xia, Ai-Bao ^{[1
]}

Luo, Shu-Ping ^{[1
]}

Tang, Jie ^{[1
]}

Zhang, Shuai ^{[1
]}

Jiang, Jun-Rong ^{[1
]}

Xu, Zhen-Yuan ^{[1
]}

机构：

[1] Zhejiang Univ Technol, State Key Lab Breeding Base Green Chem Synth Tech, Hangzhou, Zhejiang, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 21期

关键词：

asymmetric catalysis; bicyclic systems; Diels-Alder reaction; organocatalysis; water chemistry; SIMPLE ALPHA; BETA-UNSATURATED KETONES; DIARYLPROLINOL SILYL ETHER; DIRECT ALDOL REACTIONS; CHIRAL BRONSTED ACID; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; WATER; CATALYSIS; ALDEHYDES; ACCELERATION;

D O I：

10.1002/anie.200900269

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Deep-sea Diels-Alder: The asymmetric organocatalytic Diels-Alder reaction of cyclohexenones with aromatic nitroolefins can be carried out in seawater and brine. The reaction proceeds by an in situ enamine activation involving a one-step concerted addition pathway (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3821 / 3824

页数：4

共 64 条

[31] Salt effects on Diels-Alder reaction kinetics [J].

Kumar, A .

CHEMICAL REVIEWS, 2001, 101 (01) :1-19

[32] Aqueous enantioselective organocatalytic Diels-Alder reactions employing hydrazide catalysts. A new scaffold for organic acceleration [J].

Lemay, M ;

Ogilvie, WW .

ORGANIC LETTERS, 2005, 7 (19) :4141-4144

[33]

Li C.J., 1997, ORGANIC REACTION AQU

[34]

LI CJ, 2005, CHEM-EUR J, V12, P1312

[35] Stereoselective organic reactions in water [J].

Lindström, UM .

CHEMICAL REVIEWS, 2002, 102 (08) :2751-2771

[36] Enantioselective direct aza hetero-Diels-Alder reaction catalyzed by chiral Bronsted acids [J].

Liu, Hua ;

Cun, Lin-Feng ;

Mi, Ai-Qiao ;

Jiang, Yao-Zhong ;

Gong, Liu-Zhu .

ORGANIC LETTERS, 2006, 8 (26) :6023-6026

[37] The advent and development of organocatalysis [J].

MacMillan, David W. C. .

NATURE, 2008, 455 (7211) :304-308

[38]

MARUOKA K, 2000, CATALYTIC ASYMMETRIC

[39] Organocatalytic direct Michael reaction of ketones and aldehydes with β-nitrostyrene in brine [J].

Mase, N ;

Watanabe, K ;

Yoda, H ;

Takabe, K ;

Tanaka, F ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :4966-4967

[40] Catalytic asymmetric aldol reactions in aqueous media [J].

Mlynarski, Jacek ;

Paradowska, Joanna .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (08) :1502-1511

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