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European J Org Chem. 2017 Apr 18;2017(15):2130-2138. doi: 10.1002/ejoc.201700014. Epub 2017 Feb 28.

Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation.

European journal of organic chemistry

Daniel Rackl, Viktor Kais, Eugen Lutsker, And Oliver Reiser

Affiliations

  1. Institute of Organic Chemistry University of Regensburg 93053 Regensburg Germany.

PMID: 28529446 PMCID: PMC5412674 DOI: 10.1002/ejoc.201700014

Abstract

The synthesis of chiral tetrahydrofurans and pyrrolidines starting from 1,2-diols or β-amino alcohols, respectively, by visible-light-mediated deoxygenation is described. Easily accessible monoallylated/propargylated substrates were activated either as inexpensive ethyl oxalates or as recyclable 3,5-bis(trifluoromethyl)benzoates to generate alkyl radicals suitable for 5-

Keywords: Electron transfer; Heterocycles; Photocatalysis; Photochemistry; Radical reactions

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