Stereoselective synthesis of methyl (Z)-α-methoxyacrylates via two-carbon homologation of aldehydes

Rachid Baati, Charles Mioskowski, Dhurke Kashinath, Sanjeevarao Kodepelly, Biao Lu, J. R. Falck

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

Methyl (Z)-α-methoxyacrylates are generated in good yields by a mild, stereospecific two-carbon homologation of a wide variety of aldehydes utilizing commercial methyl 2,2-dichloro-2-methoxyacetate and CrCl2 under Barbier conditions at room temperature. A rational mechanism based upon a Reformatsky-type addition pathway or an in situ generated (E)-trioxo-chromium vinylidene carbenoid is proposed.

Original languageEnglish (US)
Pages (from-to)402-405
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number4
DOIs
StatePublished - Jan 28 2009

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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