Regio-and enantioselective intermolecular hydroacylation: Substrate-directed addition of salicylaldehydes to homoallylic sulfides
MM Coulter, KGM Kou, B Galligan… - Journal of the American …, 2010 - ACS Publications
Journal of the American Chemical Society, 2010•ACS Publications
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.
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.
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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