Pt(IV)-catalyzed generation and [4+2]-cycloaddition reactions of o-quinone methides

  • Radomkit S
  • Sarnpitak P
  • Tummatorn J
 et al. 
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Abstract

Novel intermolecular and intramolecular generations of ortho-quinone methides and their formal [4+2]-cycloaddition reactions with olefins catalyzed by PtCl4and AuCl3under mild conditions have been developed. Good to excellent yields (up to 99%) and diastereoselectivity (up to >99:1) of the chromans were obtained. PtCl4was found to be effective and compatible with various functional groups present in the substrates. A mechanism accounting for its catalytic cycle is proposed and discussed. © 2011 Elsevier Ltd. All rights reserved.

Author-supplied keywords

  • Chroman
  • Cycloaddition
  • Metal catalysis
  • Stereoselective
  • ortho-Quinone methide

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Authors

  • Poonsakdi PLOYPRADITHChulabhorn Research Institute

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  • Suttipol Radomkit

  • Pakornwit Sarnpitak

  • Jumreang Tummatorn

  • Paratchata Batsomboon

  • Somsak Ruchirawat

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