Premium
Efficient Construction of the Clerodane Decalin Core by an Asymmetric Morita–Baylis–Hillman Reaction/Lewis Acid Promoted Annulation Strategy
Author(s) -
Rodgen Stacy A.,
Schaus Scott E.
Publication year - 2006
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.200601076
Subject(s) - decalin , annulation , chemistry , lewis acids and bases , brønsted–lowry acid–base theory , catalysis , stereochemistry , diterpene , organocatalysis , organic chemistry , enantioselective synthesis
Linking rings : A general route toward the clerodane diterpene core using an asymmetric Morita‐Baylis‐Hillman (MBH)/Lewis acid mediated ring‐annulation process has been developed. The scope of the asymmetric Brønsted acid catalyzed MBH reaction has been expanded to include silane‐containing aldehydes, which are elaborated into the trans decalin core in high diastereo‐ and enantioselectivities.