Copper(I)-Catalyzed Highly Enantioselective [3+3]-Cycloaddition of β-Aryl/Alkyl Vinyl Diazoacetates with Nitrones

beta-Aryl/alkyl vinyl diazoacetates were investigated in metallo-vinylcarbene reactions with nitrones, revealing a Rh-2(OAc)(4)-catalyzed cyclopropene dimerization reaction and a copper(I) catalyzed [3+3]-cycloaddition of nitrones. The chiral cyclopropyl-In-SaBox ligand with copper(I) catalysis could realize the asymmetric version of the cycloaddition reaction, delivering various 3,6-dihydro-1,2-oxazine derivatives in good yield and with excellent enantioselectivity under mild conditions.

Automated summary

The study demonstrated that beta-Aryl/alkyl vinyl diazoacetates can participate in metallo-vinylcarbene reactions with nitrones, leading to a Rh-2(OAc)(4)-catalyzed cyclopropene dimerization reaction and a copper(I) catalyzed [3+3]-cycloaddition of nitrones. By employing chiral cyclopropyl-In-SaBox ligand with copper(I) catalysis, the asymmetric version of the cycloaddition reaction was achieved, delivering various 3,6-dihydro-1,2-oxazine derivatives in good yield and with excellent enantioselectivity under mild conditions.