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

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.

SUBMITTER: Rackl D

PROVIDER: S-EPMC5412674 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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

Rackl Daniel D Kais Viktor V Lutsker Eugen E Reiser And Oliver AO

European journal of organic chemistry 20170228 15

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-exo-trig/5-exo-dig cyclizations under visible-light irradiation. ...[more]

PMID: 28529446

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