An Atropos Chiral Biphenyl Bisphosphine Ligand Bearing Only 2,2′-Substituents and Its Application in Rh-Catalyzed Asymmetric Hydrogenation

Jia Jia, Zheng Ling, Zhenfeng Zhang, Ken Tamura, Ilya D. Gridnev, Tsuneo Imamoto, Wanbin Zhang

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

An atropos chiral biphenyl bisphosphine ligand bearing only 2,2′-substituents was rationally designed and easily synthesized utilizing a bulky chiral t-butylmethylphosphino block. Computational results showed a large difference in the free energies between the two diastereomers (7.8 kcal/mol) and attainable rotational energy barriers from one diastereomer to another (27.7 kcal/mol and reverse 19.9 kcal/mol). This ligand avoids the time-consuming optical resolution generally needed for the preparation of axially chiral ligands and shows high reactivity and enantioselectivity in Rh-catalyzed asymmetric hydrogenations. (Figure presented.).

Original languageEnglish
Pages (from-to)738-743
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume360
Issue number4
DOIs
Publication statusPublished - 2018 Feb 15

Keywords

  • Asymmetric hydrogenation
  • Atropos
  • Biphenyl
  • Bisphosphine ligand
  • Rh-catalyzed

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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