Catalytic Asymmetric Synthesis of Chiral Tertiary Organoboronic Esters through Conjugate Boration of β-Substituted Cyclic Enones
I-Hon Chen, Liang Yin, Wataru Itano, Motomu Kanai and Masakatsu Shibasaki*
*Graduate School of Pharmaceutical Sciences, The University
of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Email: mshibasa
mol.f.u-tokyo.ac.jp
I-H. Chen, L. Yin, W. Itano, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 2009, 131, 11284-11285.
DOI: 10.1021/ja9045839
Abstract
A catalytic enantioselective conjugate boration of β-substituted cyclic enones in the presence of a QuinoxP*-CuOtBu complex produced enantiomerically enriched tertiary organoboronates. The substrate scope was broad, and high enantioselectivity was produced using both β-aromatic and aliphatic (linear and branched)-substituted cyclic enones with five- to seven-membered ring sizes.
see article for more examples
I-H. Chen, M. Kanai, M. Shibasaki, Org. Lett., 2010, 12, 4098-4101.
Key Words
ID: J48-Y2009-2540
