Synthesis 2015; 47(20): 3153-3160
DOI: 10.1055/s-0034-1380433
paper
© Georg Thieme Verlag Stuttgart · New York

Direct Preparation of Pyrrolizidines Using Imines and Isonitriles

Isabel P. Kerschgens
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland   Email: karl.gademann@unibas.ch
,
Karl Gademann*
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland   Email: karl.gademann@unibas.ch
› Author Affiliations
Further Information

Publication History

Received: 20 March 2015

Accepted after revision: 01 May 2015

Publication Date:
09 July 2015 (eFirst)

Abstract

An acid-mediated annulation reaction for the formation of 7a-substituted unnatural pyrrolizidines is described. To reach this goal, the pyrroline 3-(3,4-dihydro-2H-pyrrol-5-yl)propan-1-ol is reacted with a large variety of isonitriles directly resulting in the target compounds. The reaction is operationally simple and tolerates air and water, and the resulting pyrrolizidines can be further transformed to the corresponding oxidized and reduced derivatives.

Supporting Information

 
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