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Regioselective Hydrosilylation of Propargylic Alcohols: An Aldol Surrogate
Author(s) -
Trost Barry M.,
Ball Zachary T.,
Jöge Thomas
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.200351587
Subject(s) - aldol reaction , hydrosilylation , regioselectivity , propargyl , chemistry , enantioselective synthesis , yield (engineering) , organic chemistry , catalysis , materials science , metallurgy
Aldol products from a non‐aldol reaction: A one‐pot protocol effects hydrosilylation of propargyl alcohols and subsequent oxidative cleavage to yield β‐hydroxy ketones in a chemo‐, regio‐, and enantioselective fashion. Further structural elaboration of the intermediate γ‐hydroxyvinylsilane is possible before the carbonyl group is unmasked (see scheme).