Enantioselective copper-catalyzed allylic substitution reaction with aminohydroxyphosphine ligand

Naohiko Yoshikai, Kotaro Miura, Eiichi Nakamura

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

A proline-derived aminohydroxyphosphine ligand induced excellent regio- and enantiose-lectivities (SN2′: SN2>94:6, 94-97% ee) in the copper-catalyzed substitution reaction of cinnamyl phosphates with Et2Zn. A computational modelling study of the reaction pathway suggests that the displacement of the leaving group takes place in an ordered, anti-fashion through simultaneous copper-olefin and zinc-oxygen interactions, which is critical for the enantioselection.

Original languageEnglish
Pages (from-to)1014-1018
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume351
Issue number7-8
DOIs
Publication statusPublished - 2009 May
Externally publishedYes

Keywords

  • Allylic substitution
  • C-C bond formation
  • Copper
  • Organozinc reagents
  • Phosphane ligands

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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