Tetrahedron

Synthesis of 2, 3-disubstituted pyrrolidines by intramolecular addition of α-aminoalkyl radicals to electron deficient C C bonds

JM Aurrecoechea, A Fernández, JM Gorgojo, C Saornil

Index: Aurrecoechea, Jose M.; Fernandez, Alvaro; Gorgojo, Jose M.; Saornil, Carlos Tetrahedron, 1999 , vol. 55, # 23 p. 7345 - 7362

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Citation Number: 40

Abstract

2, 3-Disubstituted pyrrolidines are prepared by SmI2-promoted cyclization of α-amino radicals generated from N-(α-benzotriazolylalkyl) alkenylamines containing a C C bond activated by an electron withdrawing substituent. The diastereoselectivity of cyclization is moderate and depends on the nature of the substituent at the pyrrolidine 2-position.