Radical Cyclization of Dialkyldiallylammonium Salts. A Stereoselective Route to Pyrrolidines

M. P. Bertrand; S. Gastaldi; R. Nouguier

doi:10.1055/s-1997-1043

Synlett 1997; 1997(12): 1420-1422
DOI: 10.1055/s-1997-1043

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Radical Cyclization of Dialkyldiallylammonium Salts. A Stereoselective Route to Pyrrolidines

M. P. Bertrand^* , S. Gastaldi, R. Nouguier

^*Laboratoire de Chimie Moléculaire Organique - UMR 6517 - B 562 - Faculté des Sciences St Jérôme, Av. Escadrille Normandie-Niemen - 13397 - Marseille - Cedex 20, France, FAX: (33) 4.91.67.09.44; E-mail: michele.bertrand@LCMO.u-3mrs.fr

Abstract

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3,4-Substituted pyrrolidines are formed with 80% diastereomeric excess via the addition of TsSePh to dialkyldiallylammonium salts followed by dequaternization (retro-Michael or reduction depending on the alkyl group). The temporary attachment to nitrogen of more labile groups like SiMe₃ failed in reaching high diastereomeric excess; so did the complexation of nitrogen with various Lewis acids.

ammonium salts - stereoselective radical cyclisation

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