Download PDF
Synlett 1996; 1996(2): 153-154
DOI: 10.1055/s-1996-5360
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >