1004987-40-9Relevant articles and documents
Oxazaborolidinone-catalyzed enantioselective Diels-Alder reaction of acyclic α,β-unsaturated ketones
Singh, Ram Shanker,Adachi, Shinya,Tanaka, Fumi,Yamauchi, Toyonao,Inui, Chieko,Harada, Toshiro
, p. 212 - 218 (2008/09/18)
(Chemical Equation Presented) allo-Threonine-derived O-acyl-β-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.