Scientific article
English

Copper-Catalyzed Enantioselective Intramolecular Conjugate Addition/Trapping Reactions: Synthesis of Cyclic Compounds with Multichiral Centers

Published inChemistry, vol. 13, no. 13, p. 3765-3771
Publication date2007
Abstract

The Cu-catalyzed enantioselective conjugate addition of dialkylzinc to bis-alpha,beta-unsaturated carbonyl compounds followed by the intramolecular trapping of the zinc enolate in the presence of chiral phosphoramidite ligands was investigated. Cyclic and heterocyclic compounds with multichiral centers were formed as a mixture of two diastereomers with excellent diastereoselectivities (up to 99:1) and enantioselectivities (up to 94 % ee, ee=enantiomeric excess). The stereochemistry was determined to be trans,trans for the major products and trans,cis for the minor products. The absolute configuration of the cyclic compounds was assigned by comparison with the analogous adduct derived from trans-3-nonen-2-one and Et(2)Zn or the adduct obtained through conjugate addition of Me(2)Zn to trans-1-phenyl-non-2-en-1-one. Further transformation of these cyclic products into more complex compounds is under investigation in our laboratory.

Keywords
  • Copper
  • Cyclization
  • Enolates
  • Michael addition
  • Selectivity
Citation (ISO format)
LI, Kangying, ALEXAKIS, Alexandre. Copper-Catalyzed Enantioselective Intramolecular Conjugate Addition/Trapping Reactions: Synthesis of Cyclic Compounds with Multichiral Centers. In: Chemistry, 2007, vol. 13, n° 13, p. 3765–3771. doi: 10.1002/chem.200601327
Main files (1)
Article (Published version)
accessLevelRestricted
Identifiers
Journal ISSN0947-6539
775views
10downloads

Technical informations

Creation21/06/2010 14:44:08
First validation21/06/2010 14:44:08
Update time14/03/2023 15:48:13
Status update14/03/2023 15:48:13
Last indexation29/10/2024 15:33:08
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack