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Synthesis 2009(19): 3243-3250  
DOI: 10.1055/s-0029-1216951
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Synthetic Route for Pyrrolizinone Synthesis through Functionalized C-Alkylpyrroles

Canan Unaleroglu*, Dilek Isik Tasgin, Sertan Aytac, Baris Temelli
Hacettepe University, Department of Chemistry, 06800 Ankara, Turkey
Fax: +90(312)2992163; e-Mail: canan@hacettepe.edu.tr;
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Publication History

Received 21 January 2009
Publication Date:
21 August 2009 (online)

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Abstract

Regioselective addition of pyrrole to methyl 3-aryl-2-cyanoacrylates was achieved, in high yields, with copper(II) triflate as the catalyst in toluene. C-Alkylated pyrroles afforded novel pyrrolizin-3-ones, in good to high yields and high diastereomeric ratio by an intramolecular cyclization reaction under mild reaction conditions.

Key words

pyrrole - pyrrolizine - cyclizations - Michael additions - metal triflates