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. 2010 Nov 24;132(46):16330-3.
doi: 10.1021/ja107198e. Epub 2010 Oct 29.

Regio- and enantioselective intermolecular hydroacylation: substrate-directed addition of salicylaldehydes to homoallylic sulfides

Matthew M Coulter  1 , Kevin G M Kou, Baye Galligan, Vy M Dong
Affiliations

Regio- and enantioselective intermolecular hydroacylation: substrate-directed addition of salicylaldehydes to homoallylic sulfides

Matthew M Coulter et al. J Am Chem Soc. .

Abstract

We report a Rh-catalyzed, regio- and enantioselective intermolecular olefin hydroacylation under mild conditions. Hydroacylations between homoallylic sulfides, containing a substrate-bound directing group, and salicylaldehyde derivatives occur in the presence of a spiro-phosphoramidite ligand, (R)-SIPHOS-PE, to give α-branched ketones in >20:1 selectivity and up to 97% ee. Our conditions are also applicable to the asymmetric intermolecular hydroacylation of 1,2-disubstituted olefins.

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