Synfacts 2011(1): 0023-0023  
DOI: 10.1055/s-0030-1259197
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Cyclization of Zincated Homoallylamino Nitriles to Methanopyrrolidines

Contributor(s): Victor Snieckus, Matthew O. Kitching
S. Ouizem, S. Cheramy, C. Botuha, F. Chemla*, F. Ferreira, A. Pérez-Luna
Université Pierre et Marie Curie, Paris, France
Further Information

Publication History

Publication Date:
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.