Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles

被引：300

作者：

Ishimaru, Takehisa ^{[1
]}

Shibata, Norio ^{[1
]}

Horikawa, Takao ^{[1
]}

Yasuda, Naomi ^{[1
]}

Nakamura, Shuichi ^{[1
]}

Toru, Takeshi ^{[1
]}

Shiro, Motoo ^{[2
]}

机构：

[1] Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan

[2] Rigaku Corp, Tokyo 1968666, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 22期

关键词：

allyl silanes; asymmetric catalysis; cinchona alkaloids; fluorination; silyl enol ethers;

D O I：

10.1002/anie.200800717

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Catalytic variant: Allyl silanes and silyl enol ethers 1 are good substrates for the catalytic highly enantioselective fluorodesilylation using a combination of a biscinchona alkaloid, N-fluorobenzenesulfonimide (NFSI), and base (see scheme). Pharmaceutically attractive 3-aryl-3-fluorooxindoles such as 3 can also be synthesized with high enantioselectivity. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4157 / 4161

页数：5

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