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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.