New Bisoxazaborolidinone Catalyst as Bidentate Catalyst

Significance

Inspired by previous bimetallic systems which function through double electrophilic activation of carbonyl substrates, the Shea group reports a new C ₂-symmetric bisoxazaborolidinone catalyst. Closely modeled after the known related monooxazaborolidinone, comparative ^¹³C NMR studies of DMF binding reveal that the bimetallic system is considerably more acidic. This system was then applied to the Diels-Alder reaction of ­cyclopentadiene and cinnamaldehyde to furnish the corresponding adduct in high yield and moderate ee value.