Synthesis 2015; 47(14): 2093-2099
DOI: 10.1055/s-0034-1380201
paper
© Georg Thieme Verlag Stuttgart · New York

Alkylative Amination of Biogenic Furans through Imine-to-Azaallyl Anion Umpolung

Fabian Blume
Department für Chemie, Universität zu Köln, 50939 Cologne, Germany   Email: jan.deska@uni-koeln.de
,
Mhd Haitham Albeiruty
Department für Chemie, Universität zu Köln, 50939 Cologne, Germany   Email: jan.deska@uni-koeln.de
,
Jan Deska*
Department für Chemie, Universität zu Köln, 50939 Cologne, Germany   Email: jan.deska@uni-koeln.de
› Author Affiliations
Further Information

Publication History

Received: 03 February 2015

Accepted after revision: 20 March 2015

Publication Date:
19 May 2015 (online)

Abstract

Starting from biogenic furfurals, an operationally simple and scalable condensation-umpolung-alkylation protocol was employed in the synthesis of racemic furfurylamines. Subsequent enzymatic kinetic resolution by ω-transaminase or lipase biocatalysts allows for the preparation of functionalized heterocyclic building blocks from biogenic base chemicals in optically pure form.

Supporting Information

 
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