Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2011(1): 0023-0023
DOI: 10.1055/s-0030-1259197
DOI: 10.1055/s-0030-1259197
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
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
Further Information
Publication History
Publication Date:
21 December 2010 (online)
Significance
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.