Synthesis of chiral 1,3-bis(1-(diarylphosphoryl)ethyl)-benzenes via Ir-catalyzed double asymmetric hydrogenation of bis(diarylvinylphosphine oxides)

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• 作者：Xu Liu (1)
  ZhaoBin Han (1)
  Zheng Wang (1)
  KuiLing Ding (1)
  
• 关键词：bis(diarylvinylphosphine oxide) ; iridium ; asymmetric hydrogenation ; PCP ; type chiral pincer ligands
• 刊名：SCIENCE CHINA Chemistry
• 出版年：2014
• 出版时间：August 2014
• 年：2014
• 卷：57
• 期：8
• 页码：1073-1078
• 全文大小：498 KB
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• 作者单位：Xu Liu (1)
  ZhaoBin Han (1)
  Zheng Wang (1)
  KuiLing Ding (1)
  
  1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China
  
• ISSN：1869-1870

文摘

A class of chiral 1,3-bis(diarylphosphinoethyl)benzenes, which are key intermediates for the synthesis of PCP-type chiral pincer ligands, were prepared in high diastereomeric ratios and excellent ee values via double asymmetric hydrogenation of the corresponding bis(diarylvinylphosphine oxide) substrates using a SpinPhox/Ir(I) complex as the catalyst. The hydrogenation product 5a was readily transformed into the corresponding borane-protected chiral PCP-type pincer ligand 7a with high enantiomeric excess, exemplifying a viable synthetic route to optically active chiral PCP pincer ligands.