Tuning Electronic and Steric Effects: Highly Enantioselective [4+1] Pyrroline Annulation of Sulfur Ylides with α,β-Unsaturated Imines

被引：92

作者：

Lu, Liang-Qiu ^{[1
]}

Zhang, Ji-Ji ^{[1
]}

Li, Fang ^{[1
]}

Cheng, Ying ^{[1
]}

An, Jing ^{[1
]}

Chen, Jia-Rong ^{[1
]}

Xiao, Wen-Jing ^{[1
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 26期

基金：

美国国家科学基金会;

关键词：

4+1] annulation; nitrogen heterocycles; pyrroline; sulfur; ylides; VINYL SULFONIUM SALTS; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CYCLOADDITION REACTIONS; AMINOSULFOXONIUM SALTS; MIGRATORY CYCLIZATION; CARBONYL-COMPOUNDS; N-SULFONYLIMINES; BOND FORMATION; COMPLEXES;

D O I：

10.1002/anie.201000755

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical equation presented) A change in tune: A novel [4+1] annulation between atropisomeric sulfur ylides 1 and unsaturated imines 2 was developed. The method allows the synthesis of enantioenriched pyrroline products 3 in high yield and with excellent stereocontrol. The origin of stereoinduction was primarily rationalized by a conformational analysis of the ylides. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

收藏

页码：4495 / 4498

页数：4

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