Synthesis of a Chiral Quaternary Carbon Center Bearing a Fluorine Atom: Enantio- and Diastereoselective Guanidine-Catalyzed Addition of Fluorocarbon Nucleophiles

被引：135

作者：

Jiang, Zhiyong ^{[1
]}

Pan, Yuanhang ^{[1
]}

Zhao, Yujun ^{[1
]}

Ma, Ting ^{[1
]}

Lee, Richmond ^{[1
]}

Yang, Yuanyong ^{[1
]}

Huang, Kuo-Wei ^{[1
]}

Wong, Ming Wah ^{[1
]}

Tan, Choon-Hong ^{[1
]}

机构：

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 20期

关键词：

asymmetric catalysis; fluorine; guanidine; Michael addition; transition states; BETA-KETO-ESTERS; ENANTIOSELECTIVE FLUORINATION; ASYMMETRIC FLUORINATION; BICYCLIC GUANIDINE; CONJUGATE ADDITION; ALPHA-FLUORINATION; MANNICH REACTIONS; ELECTROPHILIC FLUORINATION; 1,3-DICARBONYL COMPOUNDS; CINCHONA ALKALOIDS;

D O I：

10.1002/anie.200900964

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The perfect combination: The title reaction provides adducts having quaternary carbon centers bearing a fluorine atom with high ee and d.r. values (see scheme). The mechanism and origin of stereoselectivity were elucidated by DFT calculations. The bifunctional mode of the guanidine catalysis was demonstrated in the transition states resulting from the DFT results. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3627 / 3631

页数：5

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