Organosilicon-Promoted Reactions of Methyl α-(Bromomethyl)acrylate with Aldehydes Leading to α-Methylene-γ-lactones

Sh. Kobayashi; Masaru Yasuda; Koichi Nishio

doi:10.1055/s-1996-5360

Synlett 1996; 1996(2): 153-154
DOI: 10.1055/s-1996-5360

letter

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Organosilicon-Promoted Reactions of Methyl α-(Bromomethyl)acrylate with Aldehydes Leading to α-Methylene-γ-lactones

Shū Kobayashi^* , Masaru Yasuda, Koichi Nishio

^*Department of Applied Chemistry, Faculty of Science, Science University of Tokyo (SUT), Kagurazaka, Shinjuku-ku, Tokyo 162, Fax 3-3235-2214

Abstract

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In the presence of a catalytic amount of CuCl and a stoichiometric amount of diisopropylethylamine, methyl α-(bromomethyl)acrylate (1) reacted with trichlorosilane to afford an organosilicon intermediate (2). The intermediate reacted with aldehydes in the same pot to give the corresponding α-methylene-γ-hydroxyesters (3), which were readily converted to α-methylene-γ-lactones (4).

α-methylene-γ-lactone - organosilicon - one-pot synthesis - allylation reaction

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