%0 Journal Article %A Singh, Ram Shanker %A Adachi, Shinya %A Tanaka, Fumi %A Yamauchi, Toyonao %A Inui, Chieko %A Harada, Toshiro %D 2008 %T Oxazaborolidinone-Catalyzed Enantioselective Diels−Alder Reaction of Acyclic α,β-Unsaturated Ketones %U https://acs.figshare.com/articles/journal_contribution/Oxazaborolidinone_Catalyzed_Enantioselective_Diels_Alder_Reaction_of_Acyclic_Unsaturated_Ketones/2964682 %R 10.1021/jo702043g.s001 %2 https://acs.figshare.com/ndownloader/files/4663804 %K acyclic enone dienophiles %K reactive %K Diel %K ketone dienophiles %K enantioselective Lewis acid catalysts %K catalyst exhibits %X 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 β-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. %I ACS Publications