Enantioselective Organocatalytic Synthesis of α-Cyclopropylphosphonates through a Domino Michael Addition/Intramolecular Alkylation Reaction

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Abstract

An organocatalytic domino reaction consisting of Michael addition/intramolecular alkylation between ,-unsaturated aldehydes and bromophosphonoacetates was developed. Highly functionalised cyclopropylphosphonates containing three chiral centres, one of them quaternary, were obtained with good diastereoselectivities of up to 83:17 and very high enantioselectivities of up to 99%.
Original languageEnglish
Pages (from-to)152-163
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number1
DOIs
Publication statusPublished - 1 Jan 2014

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Keywords

  • Aldehydes
  • Cyclopropanes
  • Domino reactions
  • Michael addition
  • Organocatalysis

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