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

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Published in Synlett. 2014, vol. 25, no. 20, p. 2947-2952
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 DominoOrganocatalysisBicyclo[3.2.1]octaneβ,γ-unsaturated 1,2-keto amide
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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. https://archive-ouverte.unige.ch/unige:43001

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Deposited on : 2014-12-10

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