A selective transformation of enals into chiral γ-amino alcohols
Calow, A.D.J.; Batsanov, A.S.; Pujol, A.; Solé, C.; Fernández, E.; Whiting, A.
Professor Andrew Whiting email@example.com
A one-pot synthesis of chiral amino alcohols from α,β-unsaturated aldehydes is reported which circumvents competitive 1,2- versus 1,4-boryl addition, by means of using a sterically hindered amine-derived imine. In addition to the complete chemoselectivity, modification of the Cu(I) catalyst with readily available chiral diphosphines, such as (R)-DM-BINAP, gave the 1,4-boryl addition products with high levels of asymmetric induction.
Calow, A., Batsanov, A., Pujol, A., Solé, C., Fernández, E., & Whiting, A. (2013). A selective transformation of enals into chiral γ-amino alcohols. Organic Letters, 15(18), 4810-4813. https://doi.org/10.1021/ol4022029
|Journal Article Type||Article|
|Publication Date||Sep 20, 2013|
|Deposit Date||Nov 22, 2013|
|Publicly Available Date||May 22, 2014|
|Publisher||American Chemical Society|
|Peer Reviewed||Peer Reviewed|
Accepted Journal Article
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/ol4022029.