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

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.