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  • Title: Oxazaborolidinone-catalyzed enantioselective Diels-Alder reaction of acyclic alpha,beta-unsaturated ketones.
    Author: Singh RS, Adachi S, Tanaka F, Yamauchi T, Inui C, Harada T.
    Journal: J Org Chem; 2008 Jan 04; 73(1):212-8. PubMed ID: 18052389.
    Abstract:
    allo-Threonine-derived O-acyl-B-phenyl-oxazaborolidinones are demonstrated to be powerful and highly enantioselective Lewis acid catalysts for the Diels-Alder reaction of simple acyclic enone dienophiles, expanding the scope of ketone dienophiles and dienes. With 10 to 20 mol % of catalyst, the Diels-Alder adducts are obtained in 76-98% ee with high endo-selectivity. The catalyst exhibits high activity for the reaction with the less reactive beta-substituted dienophiles and the less reactive 1,3-cycohexadiene and 1,3-butadiene derivatives. The application of the catalysts to the Diels-Alder reaction of furan is also described.
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