Conformationally flexible biphenylphosphane ligands for Ru-catalyzed enantioselective hydrogenation

Koichi Mikami, Toshinobu Korenaga, Masahiro Terada, Takeshi Ohkuma, Trang Pham, Ryoji Noyori

Research output: Contribution to journalArticlepeer-review

226 Citations (Scopus)

Abstract

Stereomutation of a BIPHEP/RuCl2/diamine complex (shown schematically) is possible because of the conformational flexibilty of BIPHEP ligands. The result is an asymmetric activation in the Ru-catalyzed hydrogenation of carbonyl compounds to optically active alcohols. Whereas a racemic BINAP/RuCl2 complex with a chiral diamine activator gives a 1:1 mixture of two diastereomers, unequal amounts of the diastereomers can be produced from a BIPHEP/RuCl2 complex and a chiral diamine. Ar = 3,5-dimethylphenyl, BINAP = 2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl, BIPHEP = 2,2'- bis(diarylphosphanyl)biphenyl.

Original languageEnglish
Pages (from-to)495-497
Number of pages3
JournalAngewandte Chemie - International Edition
Volume38
Issue number4
DOIs
Publication statusPublished - 1999 Feb 15
Externally publishedYes

Keywords

  • Activation
  • Asymmetric catalysis
  • Atropisomerism
  • P ligands
  • Ruthenium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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