Selective One-Step Synthesis of Enantiopure cis-2,5-Disubstituted Pyrrolidines or cis-3,6-Disubstituted Piperidines from the (2R,2'R) (1,2-ethanediyl) Bis-aziridine

Sébastien Fort; Isabelle McCort; Annie Duréault; Jean-Claude Depezay

doi:10.1055/s-1997-1005

Synlett 1997; 1997(11): 1235-1236
DOI: 10.1055/s-1997-1005

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Selective One-Step Synthesis of Enantiopure cis-2,5-Disubstituted Pyrrolidines or cis-3,6-Disubstituted Piperidines from the (2R,2'R) (1,2-ethanediyl) Bis-aziridine

Sébastien Fort, Isabelle McCort, Annie Duréault^* , Jean-Claude Depezay

^*Université René Descartes, Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques associé au CNRS 45 rue des Saints-Pères, 75270 Paris Cedex 06, France, FAX: 33-1-42868387; email: dureault@bisance,citi2.fr

Abstract

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Nucleophilic ring opening of the optically active (1,2-ethanediyl) bis-aziridine 1 is dependent on the reagent and solvent. In aprotic medium cis-2,5-disubstituted pyrrolidines are formed from the opening of the aziridine ring at C-1 followed by intramolecular 5-exo-tet aminocyclization. With hydroxylated reagents in protic media, the opening takes place at C-2, leading to 3-hydroxy substituted piperidines via a 6-exo-tet cyclization process.

aziridine ring opening - cyclodimerization - Yb(OTf)₃ catalysis - alkaloids

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