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      Palladacycle-catalyzed asymmetric hydrophosphination of enones for synthesis of C*- and P*-chiral tertiary phosphines

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      Author
      Huang, Yinhua
      Pullarkat, Sumod A.
      Li, Yongxin
      Leung, Pak-Hing
      Date of Issue
      2012
      School
      School of Physical and Mathematical Sciences
      Abstract
      A highly reactive and stereoselective hydrophosphination of enones catalyzed by palladacycles for the synthesis of C*- and P*-chiral tertiary phosphines has been developed. When Ph2PH was employed as the hydrophosphinating reagent, a series of C*-chiral tertiary phosphines were synthesized (C*–P bond formation) in high yields with excellent enantioselectivities, and a single recrystallization provides access to their enantiomerically pure forms. When racemic secondary phosphines rac-R3(R4)PH were utilized, a series of tertiary phosphines containing both C*- and P*-chiral centers were generated (C*–P* bond formation) in high yields with good diastereo- and enantioselectivities. The stereoelectronic factors involved in the catalytic cycle have been revealed.
      Type
      Journal Article
      Series/Journal Title
      Inorganic chemistry
      Rights
      © 2012 American Chemical Society.
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      • SPMS Journal Articles
      http://dx.doi.org/10.1021/ic202472f
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