(Z)-α-haloacrylates: An exceptionally stereoselective preparation via Cr(II)-mediated olefination of aldehydes with trihaloacetates

D. K. Barma, Abhijit Kundu, Hongming Zhang, Charles Mioskowski, J R Falck

Research output: Contribution to journalArticle

73 Scopus citations

Abstract

(Z)-α-Fluoro-, (Z)-α-chloro-, and (Z)-α-bromoacrylates were obtained with unprecedented yield and stereocontrol (>99%) via addition of the corresponding commercial trihaloacetates to aldehydes at room temperature using stoichiometric Cr(II) salts or catalytic Cr(II) with a regeneration system. The intermediate 2,2-dihalo-3-hydroxy adducts could be isolated in good yields under conditions of limited reagent at 0 °C.

Original languageEnglish (US)
Pages (from-to)3218-3219
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number11
DOIs
StatePublished - Mar 19 2003

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of '(Z)-α-haloacrylates: An exceptionally stereoselective preparation via Cr(II)-mediated olefination of aldehydes with trihaloacetates'. Together they form a unique fingerprint.

  • Cite this