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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.

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Authors

A.D.J. Calow

A.S. Batsanov

A. Pujol

C. Solé

E. Fernández



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 Mar 29, 2024
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.





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