Asymmetric Mannich Reaction of Fluorinated Ketoesters with a Tryptophan-Derived Bifunctional Thiourea Catalyst

被引：163

作者：

Han, Xiao ^{[1
]}

Kwiatkowski, Jacek ^{[1
,3
]}

Xue, Feng ^{[1
]}

Huang, Kuo-Wei ^{[1
]}

Lu, Yixin ^{[1
,2
,3
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

[2] Natl Univ Singapore, Med Chem Program, Inst Life Sci, Singapore 117543, Singapore

[3] NUS Grad Sch Integrat Sci & Engn, Singapore, Singapore

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 41期

关键词：

asymmetric synthesis; fluorination; Mannich reaction; organocatalysis; quaternary stereocenters; BETA-KETO-ESTERS; DIRECT CONJUGATE ADDITION; ENANTIOSELECTIVE FLUORINATION; MICHAEL ADDITION; CARBONYL-COMPOUNDS; MALONATE; ORGANOCATALYSIS; HALOGENATION; NITROALKENES; ACTIVATION;

D O I：

10.1002/anie.200903635

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fluorinated quaternary stereocenters: A novel bifunctional catalyst 1 derived from natural tryptophan promoted the Mannich reaction of α-fluoro-β-ketoesters to afford fluorinated chiral molecules containing vicinal quaternary and tertiary stereogenic centers with exceptional enantioselectivity. An unprecedented α-fluoro-β -lactam was also prepared by this method (see scheme; Boc=tert-butoxycarbonyl). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7604 / 7607

页数：4

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