Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to five-, six-, and seven-membered ß-substituted cyclic enones: enantioselective construction of all-carbon quaternary stereocenters.

Journal of the American Chemical Society

PubMedID: 21495647

Kikushima K, Holder JC, Gatti M, Stoltz BM. Palladium-catalyzed asymmetric conjugate addition of arylboronic acids to five-, six-, and seven-membered ß-substituted cyclic enones: enantioselective construction of all-carbon quaternary stereocenters. J Am Chem Soc. 2011;133(18):6902-5.
The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4-addition of arylboronic acids to ß-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst prepared from Pd(OCOCF(3))(2) and a chiral pyridinooxazoline ligand yields enantioenriched products bearing benzylic stereocenters. Notably, this transformation is tolerant to air and moisture, providing a practical and operationally simple method of synthesizing enantioenriched all-carbon quaternary stereocenters.