Highly Enantio- and Diastereoselective Reactions of γ-Substituted Butenolides Through Direct Vinylogous Conjugate Additions

被引：123

作者：

Zhang, Wen ^{[3
]}

Tan, Davin ^{[1
,2
]}

Lee, Richmond ^{[1
,2
]}

Tong, Guanghu ^{[3
]}

Chen, Wenchao ^{[3
]}

Qi, Baojian ^{[3
]}

Huang, Kuo-Wei ^{[1
,2
]}

Tan, Choon-Hong ^{[3
,4
]}

Jiang, Zhiyong ^{[3
]}

机构：

[1] King Abdullah Univ Sci & Technol, Div Chem & Life Sci & Engn, Thuwal 239556900, Saudi Arabia

[2] King Abdullah Univ Sci & Technol, Catalysis Ctr, Thuwal 239556900, Saudi Arabia

[3] Henan Univ, Key Lab Nat Med & Immune Engn Henan Prov, Kaifeng 475004, Henan, Peoples R China

[4] Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 40期

关键词：

amides; asymmetric catalysis; butenolides; Michael addition; vinylogous conjugate addition; FRIEDEL-CRAFTS ALKYLATION; ALPHA-STEREOGENIC AMIDES; ALDOL REACTION; MICHAEL ADDITION; SECO-PREZIZAANE; ASYMMETRIC CATALYSIS; KETONES; TRIFLUOROMETHYLATION; ORGANOCATALYSIS; TERPENOIDS;

D O I：

10.1002/anie.201205872

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The strength of the weak: An L-tert-leucine-derived amine-thiourea catalyst (see scheme, green box) promotes the asymmetric vinylogous conjugate addition reaction between γ-aryl- and alkyl-substituted butenolides with the butenamides and enoates shown. Computational studies show the preference for the observed stereochemistry is a result of favourable weak non-bonding interactions, which stabilize the transition state. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：10069 / 10073

页数：5

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