Issue 2, 2012

β-hydroxy ketones prepared by regioselective hydroacylation

Abstract

We report an intermolecular hydroacylation of allylic alcohols with salicylaldehydes to afford β-hydroxy aryl ketones in 73–94% yields as single regioisomers. The reactivity and regioselectivity were promoted by catalytic amounts of a phosphinite that forms a dynamic covalent bond with the allylic alcohol. Hydroacylation of 1,2- and 1,1-disubstituted olefins generates β-hydroxy aryl ketones bearing tertiary and quaternary centers, respectively.

Graphical abstract: β-hydroxy ketones prepared by regioselective hydroacylation

Supplementary files

Article information

Article type
Edge Article
Submitted
02 Sep 2011
Accepted
22 Sep 2011
First published
03 Oct 2011

Chem. Sci., 2012,3, 355-358

β-hydroxy ketones prepared by regioselective hydroacylation

S. K. Murphy, M. M. Coulter and V. M. Dong, Chem. Sci., 2012, 3, 355 DOI: 10.1039/C1SC00634G

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