A.D.J. Calow
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.
Authors
A.S. Batsanov
A. Pujol
C. Solé
E. Fernández
Professor Andrew Whiting andy.whiting@durham.ac.uk
Professor
Abstract
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.
Citation
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 |
| Journal | Organic Letters |
| Print ISSN | 1523-7060 |
| Electronic ISSN | 1523-7052 |
| Publisher | American Chemical Society |
| Peer Reviewed | Peer Reviewed |
| Volume | 15 |
| Issue | 18 |
| Pages | 4810-4813 |
| DOI | https://doi.org/10.1021/ol4022029 |
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Copyright Statement
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.