E. Wada, M. Yoshinaga
Mar 1, 2004
Citations
0
Influential Citations
4
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Tandem reaction of ( E , Z )-ethyl 2-nitro-3-ethoxyacrylate ( E : Z =25:75) with δ,e-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.