Asymmetric catalysis of ene-type reaction with fluoral by chiral titanium complex: A semi-empirical and ab-initio analysis of ene reactivity

Koichi Mikami, Tomoko Yajima, Masahiro Terada, Tadafumi Uchimaru

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

The chiral titanium complex-catalyzed ene-type reaction with fluoral is shown to serve as an efficient route for the asymmetric synthesis of CF3-substituted compounds of biological and synthetic importance in extremely high enantiomeric excesses (>95% ee). The ene reactivity of trihaloacetaldehyde including fluoral is estimated in terms of the balance of LUMO energy level vs. electron density on the carbonyl carbon.

Original languageEnglish
Pages (from-to)7591-7594
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number47
DOIs
Publication statusPublished - 1993 Nov 19
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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