Download PDF
Synlett 1996; 1996(1): 39-42
DOI: 10.1055/s-1996-5316
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Diastereoselective Synthesis of Pyrrolidines by 5-Exo-trig Cyclizations of α-Amino Radicals Derived from N-(α-Benzotriazolylalkyl)alkenylamines and Samarium Diiodide

José M. Aurrecoechea* , Alvaro Fernández-Acebes
  • *Departamento de Química Orgánica, Facultad de Ciencias, Universidad del País Vasco, Apartado 644, 48080 Bilbao, Spain, FAX 34 4 4648500; E-mail: qopaufem@lg.ehu.es
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

The treatment of N-(α-benzotriazolylalkyl)alkenylamines (prepared from γ,δ-unsaturated amines, benzotriazole and aldehydes) with SmI2 generates α-amino radicals and the benzotriazolyl anion. If the alkene portion of the amine is activated by an electron withdrawing substituent an efficient 5-exo-trig radical cyclization takes place to afford mono-, 2,3- and 2,4-disubstituted pyrrolidines with moderate diastereoselectivity. In the absence of the activating group dimerization or radical reduction prevail to the exclusion of cyclization.

samarium diiodide - benzotriazole - radical cyclization - pyrrolidine

      >