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Chemistry. 2012 Oct 29;18(44):13945-8. doi: 10.1002/chem.201202504. Epub 2012 Sep 24.

A highly enantioselective synthesis of functionalized 2,3-dihydrofurans by a modified Feist-Bénary reaction.

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  • 1Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, Singapore.


Organocatalysis: a modified Feist-Bénary reaction employing acyclic β-ketoesters as the dinucleophile and (E)-β,β-bromo nitrostyrenes as the dielectrophile was developed for the asymmetric synthesis of 2,3-dihydrofurans. L-Threonine-derived tertiary amine/thiourea catalysts were found to be the most efficient catalysts, inducing the reaction in a highly enantioselective manner (TBDPS=tert-butyldiphenylsilyl).

Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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