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Regio- and Enantioselective Intermolecular Hydroacylation: Substrate-Directed Addition of Salicylaldehydes to Homoallylic Sulfides

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journal contribution
posted on 24.11.2010, 00:00 by Matthew M. Coulter, Kevin G. M. Kou, Baye Galligan, Vy M. Dong
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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