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Letter

Carbon−Carbon Bond-Forming Enantioselective Synthesis of Chiral Organosilicon Compounds by Rhodium/Chiral Diene-Catalyzed Asymmetric 1,4-Addition Reaction

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Ryo Shintani, Kazuhiro Okamoto, and Tamio Hayashi*

Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan

Org. Lett., 2005, 7 (21), pp 4757–4759

DOI: 10.1021/ol051978+

Publication Date (Web): September 22, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, thayashi@kuchem.kyoto-u.ac.jp

Abstract

A new synthetic method for chiral organosilicon compounds through a rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to β-silyl α,β-unsaturated carbonyl compounds has been developed. By employing (R,R)-Bn-bod* as a ligand, a range of arylboronic acids can be coupled with these substrates in very high enantiomeric excess. The resulting β-silyl 1,4-adducts can be converted to β-hydroxy carbonyl compounds or allylsilanes while retaining their stereochemical information.

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Published In Issue October 13, 2005
Received August 16, 2005

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Letter

Carbon−Carbon Bond-Forming Enantioselective Synthesis of Chiral Organosilicon Compounds by Rhodium/Chiral Diene-Catalyzed Asymmetric 1,4-Addition Reaction

Abstract

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Recommend & Share

Related Content

Chiral Norbornadienes as Efficient Ligands for the Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Fumaric and Maleic Compounds

High Performance of a Chiral Diene−Rhodium Catalyst for the Asymmetric 1,4-Addition of Arylboroxines to α,β-Unsaturated Ketones

Enantiomerically Pure Rhodium Complexes Bearing 1,5-Diphenyl-1,5-cyclooctadiene as a Chiral Diene Ligand. Their Use as Catalysts for Asymmetric 1,4-Addition of Phenylzinc Chloride

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