β-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of imines

Sakie Kawahara, Ayako Nakano, Tomoyuki Esumi, Yoshiharu Iwabuchi, Susumi Hatakeyama

Research output: Contribution to journalArticle

181 Citations (Scopus)

Abstract

(Matrix presented) β-Isocupreidine (β-ICD)-catalyzed asymmetric Baylis-Hillman reactions of aromatic imines with 1,1,1,3,3, 3-hexafluoroisopropyl acrylate (HFIPA) give (S)-enriched N-protected-α -methylene-β-amino acid esters. In contrast to the corresponding aldehydes, imines show the opposite enantioselectivity. A mechanistic proposal governed by hydrogen bonding is presented.

Original languageEnglish
Pages (from-to)3103-3105
Number of pages3
JournalOrganic letters
Volume5
Issue number17
DOIs
Publication statusPublished - 2003 Aug 21
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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