Asymmetric hydroformylation of unsaturated esters with PtCl(SnCl3)[(R,R)-Diop] catalyst

László Kollár, Giambattista Consiglio, Piero Pino

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Abstract

Dimethyl 2-(formylmethyl)butanedioate (2e) has been synthesized regioselectively with an enantiomeric excess of more than 82% by the homogeneous catalytic hydroformylation of dimethyl itaconate (1e) with PtCl(SnCl3)[(R,R)-DIOP] as the catalyst precursor. Under the conditions used a competitive hydrogenation to dimethyl 2-methylsuccinate (3e) takes place. This reaction occurs with an optical yield of up to 51%. For other vinylidene esters 1 the asymmetric induction was lower both in the hydroformylation and in the competitive hydrogenation. The relationship between the absolute configuration of the predominant antipodes and the possible transition states responsible for the enantioface discrimination is discussed in terms of a model developed and successfully used for olefinic hydrocarbons as substrates.

Original languageEnglish
Pages (from-to)305-314
Number of pages10
JournalJournal of Organometallic Chemistry
Volume330
Issue number1-2
DOIs
Publication statusPublished - Aug 18 1987

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ASJC Scopus subject areas

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

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