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A Designed Amide as an Aldol Donor in the Direct Catalytic Asymmetric Aldol Reaction
Author(s) -
Weidner Karin,
Kumagai Naoya,
Shibasaki Masakatsu
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201403118
Subject(s) - aldol reaction , chemistry , lewis acids and bases , catalysis , amide , enantioselective synthesis , brønsted–lowry acid–base theory , lewis acid catalysis , keto–enol tautomerism , combinatorial chemistry , organic chemistry
The direct catalytic asymmetric aldol reaction offers efficient access to β‐hydroxy carbonyl entities. Described is a robust direct catalytic asymmetric aldol reaction of α‐sulfanyl 7‐azaindolinylamide, thus affording both aromatic and aliphatic β‐hydroxy amides with high ee values. The design of this transformation features a cooperative interplay of a soft and a hard Lewis acid, which together facilitate the challenging chemoselective enolization by a hard Brønsted base.