Highly Diastereo- and Enantioselective Organocatalytic One-Pot Sequential 1,4-Addition/Dearomative-Fluorination Transformation

被引：77

作者：

Li, Feng ^{[1
]}

Sun, Long ^{[1
]}

Teng, Yuou ^{[2
]}

Yu, Peng ^{[2
]}

Zhao, John Cong-Gui ^{[3
]}

Ma, Jun-An ^{[1
]}

机构：

[1] Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R China

[2] Tianjin Univ Sci & Technol, Coll Bioengn, Tianjin 300457, Peoples R China

[3] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 45期

关键词：

1; 4-addition reactions; asymmetric catalysis; organocatalysis; pyrazolones; thiourea catalysts; ASYMMETRIC MICHAEL ADDITION; ALPHA; BETA-UNSATURATED IMIDES; OXIDATIVE DEAROMATIZATION; MEDICINAL CHEMISTRY; THIOUREA CATALYSTS; NITROOLEFINS; KETONES; HYDROGENATION; FLUORINATION; PYRAZOLONE;

D O I：

10.1002/chem.201202636

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fluorination: A wide range of nitroolefins and pyrazol-5-ones undergo a sequential 1,4-addition/dearomative-fluorination transformation when treated with a catalytic amount of a tertiary-amine-thiourea compound and the terminal electrophile, N-fluorobenzenesulfonimide, to give fluorinated products in 72-95 % yield with up to 99:1 d.r. and 98 % ee. Notably, these products contain adjacent tertiary and α-fluoro quaternary stereocenters (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：14255 / 14260

页数：6

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