Chiral, non-racemic N-(2-iodoethyl)-5-vinylpyrrolidin-2-ones have been synthesized and then cyclized with tributyltin hydride and azoisobutyronitrile (AIBN) to produce chiral, non-racemic pyrrolizidin-2-ones, with high diastereoselectivity. Reduction of the lactam moiety provides a facile route to naturally occurring pyrrolizidine alkaloids.
P. F. Keusenkothen and M. B. Smith, J. Chem. Soc., Perkin Trans. 1, 1994, 2485 DOI: 10.1039/P19940002485
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