Carbon-Carbon Bond-Forming Enantioselective Synthesis of Chiral Organosilicon Compounds by Rhodium/Chiral Diene-Catalyzed Asymmetric 1,4-Addition Reaction
Ryo Shintani, Kazuhiro Okamoto and Tamio Hayashi*
*Department of Chemistry, Graduate School of Science, Kyoto University,
Sakyo, Kyoto 606-8502, Japan, Email: thayashi
kuchem.kyoto-u.ac.jp
R. Shintani, K. Okamoto, T. Hayashi, Org. Lett., 2005, 7, 4757-4759.
DOI: 10.1021/ol051978+
Abstract
An enantioselective, rhodium-catalyzed 1,4-addition of arylboronic acids to β-silyl α,β-unsaturated carbonyl compounds has been developed employing (R,R)-Bn-bod* as a ligand, which allows the synthesis of various β-silyl 1,4-adducts in very high enantiomeric excess. Subsequent conversions of the chiral organosilicon compounds to β-hydroxy carbonyl compounds or allylsilanes under retention of the configuration of the stereogenic center are described.
see article for more examples
see article for more reactions
R. Shintani, Y. Ichikawa, K. Takatsu, F.-X. Chen, T. Hayashi, J. Org. Chem., 2009, 74, 869-873.
Key Words
Conjugate Additions, Boronic Acids, Tamao Oxidation, β-hydroxy ketones
ID: J54-Y2005-1740
