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Issue 24, 2016
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A versatile synthesis of chiral β-aminophosphines

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Abstract

A method for the preparation of chiral β-aminophosphines having substituted P-aryl groups is described. Ring-opening of cyclic sulfamidates with metal diarylphosphinites yields β-aminophosphine oxides, which are then reduced to the corresponding phosphines. Effects of the diarylphosphinite countercation on the regioselectivity of the ring-opening reaction (P- versus O-alkylation) are discussed. This method enables the introduction of electron-deficient, electron-rich and sterically hindered diarylphosphino groups, as demonstrated by the synthesis of a series of novel, P-aryl-substituted β-aminophosphines derived from tert-leucinol, valinol and phenylglycinol. Access to these derivatives will create new opportunities for steric and electronic tuning of β-aminophosphine-derived chiral ligands and organocatalysts.

Graphical abstract: A versatile synthesis of chiral β-aminophosphines

  • This article is part of the themed collection: New Talent
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Supplementary files

Article information


Submitted
27 Nov 2015
Accepted
18 Dec 2015
First published
04 Jan 2016

Org. Biomol. Chem., 2016,14, 5665-5672
Article type
Paper

A versatile synthesis of chiral β-aminophosphines

H. Y. Su, Y. Song and M. S. Taylor, Org. Biomol. Chem., 2016, 14, 5665
DOI: 10.1039/C5OB02439K

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