Cinchona Alkaloid Catalyzed Enantioselective Fluorination of Allyl Silanes, Silyl Enol Ethers, and Oxindoles | Zendy

Ishimaru Takehisa | Zendy; Shibata Norio | Zendy; Horikawa Takao | Zendy; Yasuda Naomi | Zendy; Nakamura Shuichi | Zendy; Toru Takeshi | Zendy; Shiro Motoo | Zendy

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Cinchona Alkaloid Catalyzed Enantioselective Fluorination of Allyl Silanes, Silyl Enol Ethers, and Oxindoles

Author(s) -

Ishimaru Takehisa,

Shibata Norio,

Horikawa Takao,

Yasuda Naomi,

Nakamura Shuichi,

Toru Takeshi,

Shiro Motoo

Publication year - 2008

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200800717

Subject(s) - cinchona , enol , silylation , silanes , enantioselective synthesis , catalysis , chemistry , organic chemistry , aryl , alkyl , silane

Catalytic variant : Allyl silanes and silyl enol ethers 1 are good substrates for the catalytic highly enantioselective fluorodesilylation using a combination of a bis‐cinchona alkaloid, N ‐fluorobenzenesulfonimide (NFSI), and base (see scheme). Pharmaceutically attractive 3‐aryl‐3‐fluorooxindoles such as 3 can also be synthesized with high enantioselectivity.

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