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

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

*Department of Materials Chemistry, Graduate School of Engineering, Tohoku University, Sendai 980-8579, Japan, Email: oishuaporg.che.tohoku.ac.jp

S. Oi, A. Taira, Y. Honma, Y. Inoue, Org. Lett., 2003, 5, 97-99.

DOI: 10.1021/ol0272904

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Abstract

A conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds catalyzed by a cationic rhodium complex generated from [Rh(cod)(MeCN)₂]BF₄ and (S)-BINAP in dioxane/water gave products in good yields and excellent enantioselectivities.

see article for more examples

proposed transistion states

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Conjugate Addition of Organosiloxanes to α,β-Unsaturated Carbonyl Compounds Catalyzed by a Cationic Rhodium Complex

S. Oi, Y. Honma, Y. Inoue, Org. Lett., 2002, 4, 667-669.

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Key Words

Carbonyl Compounds, Carboxylic Compounds, Arenes, Alkenes, Siloxanes

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ID: J54-Y2003-260