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

Article abstract of DOI:10.1016/S0040-4020(99)00359-2

2,3-Disubstituted pyrrolidines are prepared by SmI₂-promoted cyclization of α-amino radicals generated from N-(α- benzotriazolylakyl)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.