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Cyclization of Zincated Homoallylamino Nitriles to Methanopyrrolidines
S. Ouizem, S. Cheramy, C. Botuha, F. Chemla*, F. Ferreira, A. Pérez-Luna
Université Pierre et Marie Curie, Paris, France
21 December 2010 (online)
The cyclization of zincated α-N-homoallylamino nitriles to methanopyrrolidines is reported. Epimerization of chiral centers within the pyrrolidine ring (R² = Et) under the reaction conditions was also observed. Stereochemistry was confirmed by crystallization of the corresponding hydrochloride salts or NOE correlation spectroscopy. A mechanistic rationale to explain this result is proposed.