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Dual enantioselective Diels–Alder process in the cyclization of chiral acrylamide with dienes
Author(s) -
Jung Doo Young,
Park Doo Han,
Kim Sung Han,
Kim Yong Hae
Publication year - 2004
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.828
Subject(s) - cyclopentadiene , chemistry , lewis acids and bases , enantioselective synthesis , selectivity , diels–alder reaction , organic chemistry , stereochemistry , catalysis
Diels–Alder cycloadditions of chiral acrylamides with cyclopentadiene or 2, 3‐dimethyl butadiene proceed with high diastereofacial selectivity. Either endo‐R or endo‐S products have been obtained depending upon the structures of acrylamides and Lewis acids used. The endo form was exclusively obtained over the exo form. The dependence of the mechanism of formation of opposite configurations of endo‐R or endo‐S products on the Lewis acids is discussed. Copyright © 2004 John Wiley & Sons, Ltd.