1,4-Addition of silicon dienoates to α,β-unsaturated aldehydes catalyzed by in situ-generated silicon Lewis acid

Hikaru Yanai; Arata Takahashi; Takeo Taguchi

doi:10.1039/C0CC02438D

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1,4-Addition of silicon dienoates to α,β-unsaturated aldehydes catalyzed by in situ-generated silicon Lewis acid†

Hikaru Yanai,^a Arata Takahashi^a and Takeo Taguchi*^a

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* Corresponding authors

^a School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
E-mail: taguchi@toyaku.ac.jp
Fax: +81 42 676 3257
Tel: +81 42 676 3257

Abstract

In situ-generated silyl methide species (R₃Si–CTf₂R′) effectively catalyzed the reaction of β-substituted α,β-unsaturated aldehydes with silicon dienoates such as 3-bromo-2-TESO-furan to give the corresponding γ-adducts with excellent 1,4-selectivity and good anti selectivity.

This article is part of the themed collection: Fluorine Chemistry

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Article information

DOI: https://doi.org/10.1039/C0CC02438D
Article type: Communication
Submitted: 08 Jul 2010
Accepted: 28 Sep 2010
First published: 22 Oct 2010

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Chem. Commun., 2010,46, 8728-8730

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1,4-Addition of silicon dienoates to α,β-unsaturated aldehydes catalyzed by in situ-generated silicon Lewis acid

H. Yanai, A. Takahashi and T. Taguchi, Chem. Commun., 2010, 46, 8728 DOI: 10.1039/C0CC02438D

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Chemical Communications

1,4-Addition of silicon dienoates to α,β-unsaturated aldehydes catalyzed by in situ-generated silicon Lewis acid†

Abstract

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1,4-Addition of silicon dienoates to α,β-unsaturated aldehydes catalyzed by in situ-generated silicon Lewis acid

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