Regio- and Enantioselective Intermolecular Hydroacylation: Substrate-Directed Addition of Salicylaldehydes to Homoallylic Sulfides
journal contributionposted on 24.11.2010 by Matthew M. Coulter, Kevin G. M. Kou, Baye Galligan, Vy M. Dong
Any type of content formally published in an academic journal, usually following a peer-review process.
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.