Scientific article
English

Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents

Published inSynthesis, vol. 48, no. 19, p. 3301-3308
Publication date2016
Abstract

β-Substituted aldehydes constitute a very important class of compounds found in nature. Synthesis of this motif can be envisioned by C–C bond formation on enals. For this purpose, we report herein the development of enantioselective copper-catalyzed conjugate addition of various organometallic reagents to α,β-unsaturated aldehydes with (R)-H8BINAP, (R)-TolBINAP, and (R)-SEGPHOS as chiral ligands. Three sets of conditions were successfully developed and several enals were used. Reactivity and regio- and enantioselectivities were strongly dependent on reaction conditions and substrates. Good to excellent regio- and enantioselectivities were obtained with zinc reagents R2Zn and aluminum reagents R3Al. However, the asymmetric conjugate addition of Grignard reagents afforded only moderate to good regio- and enantioselectivities.

Keywords
  • Α,β-unsaturated aldehydes
  • Conjugate addition
  • Organometallic reagents
  • Enantioselectivity
  • Natural products
Research groups
Citation (ISO format)
CONTAL, Sylvie et al. Copper-Catalyzed Enantioselective Conjugate Addition to α,β-Unsaturated Aldehydes with Various Organometallic Reagents. In: Synthesis, 2016, vol. 48, n° 19, p. 3301–3308. doi: 10.1055/s-0035-1562487
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Article (Published version)
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Identifiers
Journal ISSN0039-7881
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