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Letter

Asymmetric 1,4-Addition of Organosiloxanes to α,β-Unsaturated Carbonyl Compounds Catalyzed by a Chiral Rhodium Complex

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Shuichi Oi,* Akio Taira, Yoshio Honma, and Yoshio Inoue*

Department of Materials Chemistry, Graduate School of Engineering, Tohoku University, Sendai 980-8579, Japan

Org. Lett., 2003, 5 (1), pp 97–99

DOI: 10.1021/ol0272904

Publication Date (Web): December 12, 2002

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

, oishu@aporg.che.tohoku.ac.jp

Abstract

Highly enantioselective 1,4-addition of organosiloxanes to α,β-unsaturated carbonyl compounds was found to be catalyzed by a chiral rhodium complex generated from [Rh(cod)(MeCN)₂]BF₄ and (S)-BINAP. Both (E)- and (Z)-1-alkenyl groups as well as aryl groups can be introduced enantioselectively into the β-position of a variety of ketones, esters, and amides.

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Published In Issue January 09, 2003
Received November 15, 2002

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Letter

Asymmetric 1,4-Addition of Organosiloxanes to α,β-Unsaturated Carbonyl Compounds Catalyzed by a Chiral Rhodium Complex

Abstract

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History

Recommend & Share

Related Content

Organo[2-(hydroxymethyl)phenyl]dimethylsilanes as Mild and Reproducible Agents for Rhodium-Catalyzed 1,4-Addition Reactions

Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl- and Alkenylboronic Acids to Enones

Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryltitanium Reagents Generating Chiral Titanium Enolates: Isolation as Silyl Enol Ethers

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