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Cinchona‐Alkaloid‐Catalyzed Enantioselective Direct Aldol‐Type Reaction of Oxindoles with Ethyl Trifluoropyruvate
Author(s) -
Ogawa Shinichi,
Shibata Norio,
Inagaki Junji,
Nakamura Shuichi,
Toru Takeshi,
Shiro Motoo
Publication year - 2007
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.200703317
Subject(s) - stereocenter , enantioselective synthesis , trifluoromethyl , chemistry , cinchona , enantiomer , aldol reaction , organic chemistry , organocatalysis , alcohol , cinchona alkaloids , moiety , stereochemistry , combinatorial chemistry , alkyl , catalysis
One or t'other : Pseudoenantiomeric cinchona alkaloids can be used as organocatalysts to access both enantiomeric products of the title reaction selectively in high yields with high diastereo‐ and enantioselectivities (up to 99 % ee ; see scheme). One of the two contiguous quaternary stereogenic carbon centers that are constructed simultaneously is a pharmaceutically significant tertiary α‐trifluoromethyl alcohol center. R 1 =alkyl; R 2 =H, Me.