Highly regioselective addition of an ester enolate equivalent to α,β-unsaturated ketones: selective formation of both isomers derived from 1,2- and 1,4-additions using α-stannyl ester with additives

Makoto Yasuda; Yozo Matsukawa; Keishi Okamoto; Toshifumi Sako; Noriko Kitahara; Akio Baba

doi:10.1039/B004817H

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Highly regioselective addition of an ester enolate equivalent to α,β-unsaturated ketones: selective formation of both isomers derived from 1,2- and 1,4-additions using α-stannyl ester with additives

Makoto Yasuda,^a Yozo Matsukawa,^a Keishi Okamoto,^a Toshifumi Sako,^a Noriko Kitahara^a and Akio Baba*^a

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* Corresponding authors

^a Department of Applied Chemistry, Faculty of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka, Japan.
E-mail: baba@ap.chem.eng.osaka-u.ac.jp

Abstract

The reaction of α-stannyl ester with α,β-unsaturated ketones in the presence of stannous chloride (SnCl₂) and chlorosilanes (Me₃SiCl or Me₂SiCl₂) gave 1,2- and 1,4-addition products, respectively.

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Article information

DOI: https://doi.org/10.1039/B004817H
Article type: Communication
Submitted: 15 Jun 2000
Accepted: 26 Sep 2000
First published: 19 Oct 2000

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Chem. Commun., 2000, 2149-2150

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Highly regioselective addition of an ester enolate equivalent to α,β-unsaturated ketones: selective formation of both isomers derived from 1,2- and 1,4-additions using α-stannyl ester with additives

M. Yasuda, Y. Matsukawa, K. Okamoto, T. Sako, N. Kitahara and A. Baba, Chem. Commun., 2000, 2149 DOI: 10.1039/B004817H

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Chemical Communications

Highly regioselective addition of an ester enolate equivalent to α,β-unsaturated ketones: selective formation of both isomers derived from 1,2- and 1,4-additions using α-stannyl ester with additives

Abstract

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Highly regioselective addition of an ester enolate equivalent to α,β-unsaturated ketones: selective formation of both isomers derived from 1,2- and 1,4-additions using α-stannyl ester with additives

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