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Scientific article
English

Highly Enantioselective One-Pot Copper-Catalyzed 1,4 Addition/Organocatalyzed α-Substitution of Enals

Published inAdvanced synthesis & catalysis, vol. 352, no. 11-12, p. 1856-1860
Publication date2010
Abstract

The asymmetric copper-catalyzed addition of dialkylzinc to enals followed by organocatalyzed one-pot aldehyde α-functionalization has been accomplished providing CC, CCl or CF bond formation. These simple procedures led to the creation of two contiguous stereocenters in excellent enantioselectivities (typical ee=99%). This methodology has been applied in the synthesis of (2S,3S) isomer of Valnoctamide®.

Keywords
  • Copper
  • Enals
  • Enantioselectivity
  • Michael addition
  • Organocatalysis
Citation (ISO format)
QUINTARD, Adrien, ALEXAKIS, Alexandre. Highly Enantioselective One-Pot Copper-Catalyzed 1,4 Addition/Organocatalyzed α-Substitution of Enals. In: Advanced synthesis & catalysis, 2010, vol. 352, n° 11-12, p. 1856–1860. doi: 10.1002/adsc.201000309
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Article (Published version)
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Identifiers
ISSN of the journal1615-4150
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Technical informations

Creation09/30/2010 11:19:00 AM
First validation09/30/2010 11:19:00 AM
Update time03/14/2023 4:06:59 PM
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