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Scientific article
English

Direct Organocatalytic Construction of Bicyclo[3.2.1]octanes by Domino Michael/Aldol Reaction with β,γ-Unsaturated 1,2-Keto Amides

Published inSynlett, vol. 25, no. 20, p. 2947-2952
Publication date2014
Abstract

A direct construction of bicyclo[3.2.1]octanes by an organocatalytic domino Michael/Aldol reaction of cyclic 1,3-keto esters with β,γ-unsaturated 1,2-keto amides is reported. Formation of a precipitate corresponding to the racemic co-crystals of the bicyclic compound was observed in toluene, whereas a homogeneous solution was obtained in dichloromethane. Preliminary mechanistic investigations on the reversibility of the system allowed enhancing the selectivity (>20:1 dr, 73% ee). Relative configuration of the bicyclic compound was determined by X-ray crystal structure analyses.

Keywords
  • Domino
  • Organocatalysis
  • Bicyclo[3.2.1]octane
  • β,γ-unsaturated 1,2-keto amide
Citation (ISO format)
LEFRANC, Alice et al. Direct Organocatalytic Construction of Bicyclo[3.2.1]octanes by Domino Michael/Aldol Reaction with β,γ-Unsaturated 1,2-Keto Amides. In: Synlett, 2014, vol. 25, n° 20, p. 2947–2952. doi: 10.1055/s-0034-1378901
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ISSN of the journal0936-5214
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Creation12/05/2014 3:00:00 PM
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