Premium
Synthesis of Highly Functionalized Chiral Cyclopentanes by Catalytic Enantio‐ and Diastereoselective Double Michael Addition Reactions
Author(s) -
Zu Liansuo,
Li Hao,
Xie Hexin,
Wang Jian,
Jiang Wei,
Tang Yun,
Wang Wei
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.200700485
Subject(s) - cyclopentanes , stereocenter , michael reaction , trimethylsilyl , ether , catalysis , chemistry , double bond , organocatalysis , organic chemistry , stereochemistry , combinatorial chemistry , enantioselective synthesis
Do a double take : A novel highly enantio‐ and diastereoselective cascade double Michael reaction, in which two CC bonds and three contiguous stereogenic centers are formed, has been developed. The one‐pot process, which was efficiently catalyzed by the chiral diphenylprolinyl trimethylsilyl (TMS) ether, is a facile approach to synthetically useful chiral cyclopentanes (see scheme).