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

Rackl, Daniel and Kais, Viktor and Lutsker, Eugen and Reiser, Oliver (2017) Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (15). pp. 2130-2138. ISSN 1434-193X, 1099-0690

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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.

Item Type: Article
Uncontrolled Keywords: ENANTIOSELECTIVE SYNTHESIS; PHOTOREDOX CATALYSIS; LEONTOPODIUM-ALPINUM; ALCOHOLS; ALKENOLS; OXALATES; COMPLEX; SYSTEM; ALKYL; Photocatalysis; Photochemistry; Radical reactions; Heterocycles; Electron transfer
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 14 Dec 2018 13:10
Last Modified: 11 Feb 2019 13:58
URI: https://pred.uni-regensburg.de/id/eprint/1027

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