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Catalytic Enantioselective Aldol Reactions of Unprotected Carboxylic Acids under Phosphine Oxide Catalysis
Author(s) -
Kotani Shunsuke,
Yoshiwara Yusaku,
Ogasawara Masamichi,
Sugiura Masaharu,
Nakajima Makoto
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201810599
Subject(s) - aldol reaction , enantioselective synthesis , phosphine oxide , chemistry , catalysis , aldehyde , ketone , lewis acids and bases , organic chemistry , phosphine , carboxylic acid
The first catalytic enantioselective aldol reaction of various unprotected carboxylic acids is described. In the presence of a chiral bis(phosphine oxide) as a Lewis base catalyst, carboxylic acids were activated with silicon tetrachloride to form the corresponding bis(trichlorosilyl)enediolates in situ, which subsequently underwent an aldol reaction with an aldehyde or a ketone to produce β‐hydroxycarboxylic acids in high enantioselectivities of up to 92 % ee .