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Synlett 2011(19): 2852-2856  
DOI: 10.1055/s-0031-1289544
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 1,2,3-Trisubstituted Pyrrolidines and 2,3-Disubstituted Tetrahydrofurans via Diastereoselective Reductive Cyclization of γ-Chloroimines and γ-Chloroketones

Mudiganti Naga Venkata Sastry, Sven Mangelinckx, Bart Lucas, Norbert De Kimpe*
Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
Fax: +32(9)2646221; e-Mail: norbert.dekimpe@ugent.be;
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Publication History

Received 16 August 2011
Publication Date:
19 October 2011 (online)

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Abstract

A new diastereoselective synthetic approach towards 1,2,3-trisubstituted pyrrolidines and 2,3-disubstituted tetrahydrofurans is described. The synthesis of the pyrrolidines involves reductive cyclization of γ-chloroketimines, which were generated in situ from the reaction of 3-substituted 5-chloro-2-pentanones and a primary amine. Various reduction conditions were explored to induce a diastereoselective reductive cyclization. 2,3-Disubstituted tetrahydrofurans were obtained by the direct reduction of 3-substituted 5-chloro-2-pentanones with sodium borohydride.

Key words

pyrrolidines - tetrahydrofurans - cyclization - halo­imines - haloketones

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1

Postdoctoral Fellow of the Research Foundation-Flanders (FWO).