%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