A new strategy of tandem transetherification–intramolecular hetero Diels–Alder reaction with ( E, Z)-mixture of ethyl 2-nitro-3-ethoxyacrylate and δ,ε-unsaturated alcohols leading to functionalized trans-fused bicyclic nitronates

Abstract

Tandem reaction of ( E, Z)-ethyl 2-nitro-3-ethoxyacrylate ( E: Z=25:75) with δ,ε-unsaturated alcohols leading to functionalized trans-fused bicyclic nitronates as single stereoisomers in high yields has been developed under thermal condition and in the presence of a catalytic amount of a Lewis acid catalyst such as Yb(OTf) 3. This process involves the configurational control of transetherified intermediates under a rapid, reversible transetherification reaction pathway for affording stereoselective trans-fused cyclic nitronates as single stereoisomers in intramolecular hetero Diels–Alder reaction.