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Communication | Regular issue | Vol 23, No. 9, 1985, pp.2229-2235
Published online, 1st January, 1970
DOI: 10.3987/R-1985-09-2229
N-Vinyl-2-ethoxypyrrolidinimium Tetrafluoborate: A Novel Enophile and Synthetic Equivalent for N-Vinylpyrrolidiniminium

Michael B. Smith* and Hitesh N. Shroff

*Department of Chemistry, U-60, Rm.151, 215 Glenbrok Rd., University of Connecticut, Storrs, CT 06269-3060, U.S.A.


Cycloaddition of N-vinyl-2-ethoxypyrrolidiniminium tetrafluoborate, 3, with alkenes, followed by hydride reduction, yields the 8-alkyloctahydroindolizines, 7 and 8 which would be derived from N-vinylpyrrolidiniminium, 2. This cycloaddition-reductive elimination sequence offers a new route to indolizidine type alkaloids.