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Asymmetric Synthesis and Application of Homologous Pyrroline‐2‐alkylboronic Acids: Identification of the B–N Distance for Eliciting Bifunctional Catalysis of an Asymmetric Aldol Reaction.
Author(s) -
Batsanov Andrei S.,
Georgiou Irene,
Girling P. Ricardo,
Pommier Laure,
Shen Hong C.,
Whiting Andrew
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300127
Subject(s) - chemistry , bifunctional , aldol reaction , catalysis , enantioselective synthesis , lewis acids and bases , lewis acid catalysis , combinatorial chemistry , boronic acid , intramolecular force , acetone , organocatalysis , synergistic catalysis , organic chemistry , stereochemistry
Abstract Homoboroproline has been shown to be an efficient bifunctional catalyst for the aldol reaction of acetone with p ‐nitrobenzaldehyde by using in situ Lewis acid tuning of the boronic acid esterification with a diol. Herein, asymmetric syntheses of homologues of this catalyst are developed to compare their catalytic capability and chemical properties with homoboroproline, and to probe the effect that chain‐length separation of the amino and boronate groups has on the intramolecular B–N coordination, as well as other cooperative interactions, to explain their widely differing catalytic properties.