Aminohydroxyphosphine ligand for the copper-catalyzed enantioselective conjugate addition of organozinc reagents

Alakananda Hajra, Naohiko Yoshikai, Eiichi Nakamura

Research output: Contribution to journalArticlepeer-review

62 Citations (Scopus)

Abstract

An alanine-derived aminohydroxyphosphine ligand was developed for copper-catalyzed asymmetric conjugate addition of organozinc reagents to α,β-unsaturated carbonyl compounds. This new tridentate ligand induces consistently high enantioselectivity in reactions of a variety of acyclic substrates. Theoretical mechanistic analysis suggests that the C-C bond formation takes place through a highly ordered transition state by the coordination of the phosphorus and nitrogen atoms to the copper(III) and zinc(II) atoms, respectively, and of the oxygen anion to both the metal centers.

Original languageEnglish
Pages (from-to)4153-4155
Number of pages3
JournalOrganic letters
Volume8
Issue number18
DOIs
Publication statusPublished - 2006 Aug 31
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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