T. Matsui, S. Kitajima, M. Nakayama
1988
Citations
0
Influential Citations
5
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
A Diels–Alder reaction of methyl 2-oxo-2H-pyran-5-carboxylate (1) with isoprene gave two stereoisomers, methyl 8-methyl-8-vinyl- and 8-isopropenyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-ene-6-carboxylates. On the other hand, only a stereoisomer from a reaction of 1 with 2-methoxy-1,3-butadiene, methyl 8-methoxy-8-vinyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-ene-6-carboxylate was obtained. The stereostructures of these adducts were determined by NMR spectral data and single-crystal X-ray analyses.