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Models for the Carbonyl–ene Cyclization Reaction: Open and Closed Transition States
Author(s) -
Braddock D. Christopher,
Hii King Kuok Mimi,
Brown John M.
Publication year - 1998
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/(sici)1521-3773(19980703)37:12<1720::aid-anie1720>3.0.co;2-w
Subject(s) - ene reaction , chemistry , lewis acids and bases , transition state , medicinal chemistry , catalysis , stereochemistry , organic chemistry
Different cyclization products are formed with different Lewis acids in the ene cyclization of 5‐hexenals (see scheme on the right; a: methylaluminum bisphenoxide, b: Me 2 AlCl, c: Sc(OSO 2 CF 3 ) 3 ). This is not surprising, but it is gratifying that these result can be rationalized with an internally consistent model.