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  • Title: An organocatalytic approach to enantiomerically enriched α-arylcyclohexenones and cyclohexanones.
    Author: Duce S, Jorge M, Alonso I, García Ruano JL, Cid MB.
    Journal: Org Biomol Chem; 2011 Dec 21; 9(24):8253-60. PubMed ID: 22041709.
    Abstract:
    The presence of a p-nitrophenyl group converts acetone into an excellent and versatile nucleophile in organocatalytic processes, able to react with α,β-unsaturated aldehydes affording β-substituted α-arylcyclohexenones via a Michael reaction/aldol reaction/dehydration sequence, which occurs in good yields, ee up to 96% and complete diastereoselectivity. The resulting compounds are excellent synthons for the diastereoselective preparation of a variety of synthetically useful polysubstituted cyclohexanones and derivatives.
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