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Stereoselective Simmons–Smith Cyclopropanation of Chiral Enamides
Author(s) -
Song Zhenlei,
Lu Ting,
Hsung Richard P.,
AlRashid Ziyad F.,
Ko Changhong,
Tang Yu
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.200700681
Subject(s) - cyclopropanation , stereoselectivity , combinatorial chemistry , chemistry , stereochemistry , organic chemistry , catalysis
Efficient and practical access to chiral aminocyclopropanes is secured by the title reaction (see example). Both E and Z enamides undergo the cyclopropanation with high diastereoselectivity (d.r. up to >95:5). The application of this methodology to the synthesis of biologically significant aminocyclopropanes illustrates the potential of chiral enamides as useful building blocks for stereoselective organic synthesis.