A Michael addition and alkylation sequence using m methyl 2-(trimethylsily)-propenoate. Stereoselective synthesis of α-silyl esters

J. Tanaka, S. Kanemasa, Y. Ninomiya, O. Tsuge

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Michael addition of organomagnesiums or -lithiums with methyl 2-(trimethylsilyl)propenoate leads to either 1:1 or 1:2 adduct anions, depending upon the reaction condition and the reactivity of donor molecules. The adduct anions, both 1:1 and 1:2 types, are quenched with alkyl halides or water in a highly stereoselective manner to produce α-silylated esters. A rigid intramolecular chelation working in the adduct anions is partly responsible for the high selectivity.

Original languageEnglish
Pages (from-to)476-483
Number of pages8
JournalBulletin of the Chemical Society of Japan
Volume63
Issue number2
DOIs
Publication statusPublished - 1990

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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