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.
Professor Andrew Whiting firstname.lastname@example.org
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.
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|
|Peer Reviewed||Peer Reviewed|
|Keywords||Aldol reaction, Aminoboronic acids, Asymmetric catalysis, Bifunctional catalysis, Secondary amines.|