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Scientific article
English

Copper-Catalyzed Asymmetric Conjugate Addition with Chiral SimplePhos Ligands

Published inChemistry, vol. 15, no. 40, p. 10473-10485
Publication date2009
Abstract

SimplePhos ligands represent a novel class of monodentate chiral ligands based on a chiral amine moiety and flexible diaryl groups on the phosphorous atom. They can be easily prepared by two different pathways and they can be highly functionalised. Herein we report the copper-catalysed asymmetric conjugate addition of diethyl zinc and trialkylaluminium reagents with SimplePhos ligands, which gives high enantioselectivity with cyclic enones, acyclic enones and nitro-olefins, with up to 98.6% ee. Of particular interest is the reaction of trialkylaluminium reagents with a wide range of 3-substituted enones, thus allowing the formation of stereogenic quaternary carbon centres.

Keywords
  • Asymmetric catalysis
  • Conjugate addition
  • Copper
  • Enones
  • P ligands
Citation (ISO format)
PALAIS, Laetitia, ALEXAKIS, Alexandre. Copper-Catalyzed Asymmetric Conjugate Addition with Chiral SimplePhos Ligands. In: Chemistry, 2009, vol. 15, n° 40, p. 10473–10485. doi: 10.1002/chem.200901577
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ISSN of the journal0947-6539
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