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On the Mechanism of the Anionic Oxy‐Cope Rearrangement of trans ‐1,2‐Dialkenylcyclobutanols
Author(s) -
Maurin Philippe,
Kim SeHo,
Cho Sung Yun,
Cha Jin Kun
Publication year - 2003
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.200350988
Subject(s) - steric effects , chemistry , mechanism (biology) , selectivity , propenyl , stereochemistry , medicinal chemistry , organic chemistry , catalysis , philosophy , epistemology
A concerted mechanism involving a chairlike transition state (see scheme) and no appreciable loss of enantiopurity was concluded for the anionic oxy‐Cope rearrangement of sterically unencumbered trans ‐1,2‐dialkenylcyclobutanols from a study employing nonracemic substrates containing vinyl and propenyl groups with evaluation of the enantio‐ and diastereofacial selectivity.