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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: thayashikuchem.kyoto-u.ac.jp

R. Shintani, K. Okamoto, T. Hayashi, Org. Lett., 2005, 7, 4757-4759.

DOI: 10.1021/ol051978+ (free Supporting Information)


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.

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Tuning the Chiral Environment of C2-Symmetric Diene Ligands: Development of 3,7-Disubstituted Bicyclo[3.3.1]nona-2,6-dienes

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