Synthesis of P-Chiral Phosphine Ligands and Their Applications in Asymmetric Catalysis

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  • Imamoto Tsuneo
    Research and Development Division, Nippon Chemical Industrial Co., Ltd. Graduate School of Science, Chiba University
  • Sugiya Masashi
    Research and Development Division, Nippon Chemical Industrial Co., Ltd.
  • Oohara Nobuhiko
    Research and Development Division, Nippon Chemical Industrial Co., Ltd.
  • Tamura Ken
    Research and Development Division, Nippon Chemical Industrial Co., Ltd.

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Other Title
  • P-キラルホスフィン配位子の合成と触媒的不斉合成への利用
  • P-キラルホスフィン ハイイシ ノ ゴウセイ ト ショクバイテキ フセイ ゴウセイ エ ノ リヨウ

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Abstract

This review describes the recent progress of the synthesis of P-chiral phosphine ligands and their applications in transition-metal-catalyzed asymmetric reactions. Many enantiomerically pure P-chiral phosphine ligands have been prepared by the use of phosphine-boranes as the intermediates. Among the ligands prepared hitherto, the bidentate ligands with tert-butyl groups at the phosphorus atoms exhibit remarkably high enantioinduction ability in many catalytic asymmetric reactions, particularly in rhodium-catalyzed hydrogenations. Both enantiomers of air-stable ligands, QuinoxP* and BenzP*, are produced via (R)- and (S)-tert-butylmethylphosphine-boranes. These two ligands have been successfully used not only in asymmetric hydrogenations but also in enantioselective carbon-carbon or carbon-heteroatom bond-forming reactions. Many other P-chiral phosphine ligands reported since 2001 are also described.

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