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Enantio‐ and Diastereoselective Hydrogenation of Farnesol and O‐Protected Derivatives: Stereocontrol by Changing the CC Bond Configuration
Author(s) -
Wang Aie,
Wüstenberg Bettina,
Pfaltz Andreas
Publication year - 2008
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.200705521
Subject(s) - farnesol , allylic rearrangement , trifluoromethyl , chemistry , iridium , catalysis , stereochemistry , medicinal chemistry , organic chemistry , alkyl
Four isomers–one catalyst : The four stereoisomers of hexahydrofarnesol can be prepared with high enantio‐ and diastereoselectivity by using the same chiral iridium catalyst 1 with different cis/trans isomers of farnesol (see scheme; BAr F =tetrakis[bis‐3,5‐(trifluoromethyl)phenyl]borate). Both the internal trialkyl‐substituted CC bond and the allylic alcohol unit are hydrogenated with high facial selectivity.