Carbonylation (hydroformylation and hydrocarbalkoxylation) and enantioselective carbonylation of some methacrylic acid derivatives

Giambattista Consiglio, László Kollár, Robert Kölliker

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

The hydroformylation of methyl methacrylate (1) or t-butyl methacrylate (2) takes place with fair to good chemoselectivity, the regioselectivity depending on the catalyst precursor used. By contrast, methacrylonitrile (3), methacrylamide (4), and N-benzyl-methacrylamide (5) undergo hydroformylation followed by subsequent reactions. The formyl product formed is reduced to the corresponding 2-cyano-2-methylpropan-1-ol in the case of 3, and undergoes cyclization to 2-methyl-2,3-dehydrobutyrolactames for 4 and 5. Under conditions of hydrocarbalkoxylation in the presence of palladium catalysts, 4 gives 3-methylsuccinimide. In the enantioselective reactions, extents of asymmetric induction of about 20-50% have been obtained.

Original languageEnglish
Pages (from-to)375-383
Number of pages9
JournalJournal of Organometallic Chemistry
Volume396
Issue number2-3
DOIs
Publication statusPublished - Oct 16 1990

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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