Fe/Cr- and Co/Cr-mediated catalytic asymmetric 2-haloallylations of aldehydes

Michio Kurosu, Mei-Huey Lin, Yoshito Kishi

Research output: Contribution to journalArticle

79 Citations (Scopus)

Abstract

The first example to couple aldehydes and 3-bromo-2-halopropenes in a catalytic asymmetric manner is reported. The coupling reaction is effected by the use of a chiral sulfonamide-Cr complex (prepared in situ from 1d, CrBr3, Fe(III) or from Co(II), Et3N, and Mn), TMSCl, and 2,6-lutidine. The method reported here is operationally simple and scalable, furnishing 3-halohomoallylic alcohols with a synthetically useful level of enantiomeric excess.

Original languageEnglish
Pages (from-to)12248-12249
Number of pages2
JournalJournal of the American Chemical Society
Volume126
Issue number39
DOIs
Publication statusPublished - 2004 Oct 6

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Sulfonamides
Aldehydes
Alcohols
2,6-lutidine

All Science Journal Classification (ASJC) codes

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

Cite this

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abstract = "The first example to couple aldehydes and 3-bromo-2-halopropenes in a catalytic asymmetric manner is reported. The coupling reaction is effected by the use of a chiral sulfonamide-Cr complex (prepared in situ from 1d, CrBr3, Fe(III) or from Co(II), Et3N, and Mn), TMSCl, and 2,6-lutidine. The method reported here is operationally simple and scalable, furnishing 3-halohomoallylic alcohols with a synthetically useful level of enantiomeric excess.",
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Fe/Cr- and Co/Cr-mediated catalytic asymmetric 2-haloallylations of aldehydes. / Kurosu, Michio; Lin, Mei-Huey; Kishi, Yoshito.

In: Journal of the American Chemical Society, Vol. 126, No. 39, 06.10.2004, p. 12248-12249.

Research output: Contribution to journalArticle

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