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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

Batsanov, A.S.; Georgiou, I.; Girling, P.R.; Pommier, L.; Shen, H.C.; Whiting, A.

Authors

A.S. Batsanov

I. Georgiou

P.R. Girling

L. Pommier

H.C. Shen



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.

Citation

Batsanov, A., Georgiou, I., Girling, P., Pommier, L., Shen, H., & Whiting, A. (2014). 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. Asian Journal of Organic Chemistry, 3(4), 470-479. https://doi.org/10.1002/ajoc.201300127

Journal Article Type Article
Publication Date Apr 22, 2014
Deposit Date Nov 22, 2013
Journal Asian Journal of Organic Chemistry
Print ISSN 2193-5807
Electronic ISSN 2193-5815
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 3
Issue 4
Pages 470-479
DOI https://doi.org/10.1002/ajoc.201300127
Keywords Aldol reaction, Aminoboronic acids, Asymmetric catalysis, Bifunctional catalysis, Secondary amines.


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