Enantioselective, high-yielding synthesis of alcohol-functionalized diphosphanes utilizing asymmetric control with a chiral auxiliary

Sumod A. Pullarkat, Yuen Lin Cheow, Yongxin Li, Pak Hing Leung

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14 Citations (Scopus)

Abstract

Enantiomerically pure, alcohol-functionalized diphosphane ligands carrying one phosphorus and three carbon stereo-genie centers were generated from the Diels-Alder reactions of phosphane-functionalized terminal alkenols [3-(diphenyl-phosphanyl)but-3-en-l-ol and 2-(diphenylphosphanyl)prop-2-en-l-ol] with 3,4-dimethyl-l-phenyl-1H-phosphole. The reactions were promoted and controlled by the organoplati-num complex containing ortho-metalated (R)-[1-(dimeth-ylamino)ethyl]naphthalene, and both cycloadditions showed excellent regio- and stereoselectivity under mild conditions with only one enantiomer being formed. The products were isolated in high yield and were characterized by single-crystal X-ray diffraction analysis. Their structures in solution were analyzed by 2D 1H-1H ROESY NMR spectroscopy. Subsequent decomplexation and repreparation of the products proved the optical purity of the alcohol-functionalized, chiral diphosphanes formed.

Original languageEnglish
Pages (from-to)2375-2382
Number of pages8
JournalEuropean Journal of Inorganic Chemistry
Issue number16
DOIs
Publication statusPublished - Jun 2009
Externally publishedYes

Keywords

  • Asymmetric synthesis
  • Chiral auxiliaries
  • Cycloaddition
  • P ligands
  • Platinum

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