Asymmetric Baylis-Hillman reactions using chiral 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes catalysts under high pressure conditions

Tohru Oishi, Hiroki Oguri, Masahiro Hirama

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Abstract

Chiral C2-symmetric 2,3-disubstituted 1,4-diazabicyclo[2.2.2]octanes (DABCOs) (1) have been utilized as catalysts for asymmetric Baylis-Hillman reactions. Optically active α-methylene-β-hydroxyalkanone was obtained in up to 47% ee. Under high pressure conditions, a remarkable enhancement of both reaction rate and enantioselectivity has been observed.

Original languageEnglish
Pages (from-to)1241-1244
Number of pages4
JournalTetrahedron: Asymmetry
Volume6
Issue number6
DOIs
Publication statusPublished - Jan 1 1995
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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