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Synlett 1996; 1996(1): 39-42
DOI: 10.1055/s-1996-5316
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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
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Publikationsdatum:
31. Dezember 2000 (online)

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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