Highly efficient and practical optical resolution of 2-amino-2'-hydroxy- 1,1'-binaphthyl by molecular complexation with N-benzylcinchonidium chloride: A direct transformation to binaphthyl amino phosphine

Kuiling Ding, Yang Wang, Hongying Yun, Jinxia Liu, Yangjie Wu, Masahiro Terada, Yasutaka Okubo, Koichi Mikami

Research output: Contribution to journalArticlepeer-review

119 Citations (Scopus)

Abstract

A new type of N,P chiral ligand, binaphthyl amino phosphine 1 was synthesized through a simple and practical resolution of racemic 2-amino-2'- hydroxy-1,1'-binaphthyl by molecular complexation with 0.5 equivalents of N- benzylcinchonidium chloride in the solid state. The present procedure represents the first example of the optical resolution of amino alcohol with the use of a chiral ammonium salt as a resolving reagent. The resolution mechanism is discussed in terms of molecular recognition in solid state. The chlorine anion in N-benzylcinchonidium chloride provides the bridging link between two amino alcohol molecules [(+)-2] and the cinchonoid cation located in between, by hydrogen bonding with the surrounding moieties.

Original languageEnglish
Pages (from-to)1734-1737
Number of pages4
JournalChemistry - A European Journal
Volume5
Issue number6
DOIs
Publication statusPublished - 1999
Externally publishedYes

Keywords

  • Amino alcohols
  • Biaryls
  • Molecular recognition
  • N,P ligands
  • Optical resolution

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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