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

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



Abstract

The synthesis of chiral tetrahydrofurans and pyrrolidines starting from 1,2-diols or -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-exo-trig/5-exo-dig cyclizations under visible-light irradiation.


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