Synthesis 2002(16): 2450-2456
DOI: 10.1055/s-2002-35220
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 2,3-Dihydropyrrolizines from Weinreb 3-(Pyrrolidin-2-ylidene­)propionamides or Weinreb N-Vinylprolinamides

Luis Calvo, Alfonso González-Ortega*, M. Carmen Sañudo
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, 47005, Spain
Fax: +34(983)423013; e-Mail: algon@qo.uva.es;
Further Information

Publication History

Received 2 July 2002
Publication Date:
04 November 2002 (online)

Abstract

Weinreb 3-(pyrrolidin-2-ylidene)propionamides and Weinreb N-vinylprolinamides were used for the synthesis of 2,3-dihydropyrrolizines. The selective reaction of the carboxamide group with organometallic compounds allowed us to obtain a great variety of carbonyl intermediates, analogous to the Hantzsch and Knorr pyrrole synthesis, which were thermally cyclized.