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Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization.

ABSTRACT: 1,1-Disubstituted styrenes with internal oxygen and nitrogen nucleophiles undergo oxidative fluorocyclization reactions with in situ generated chiral iodine(III)-catalysts. The resulting fluorinated tetrahydrofurans and pyrrolidines contain a tertiary carbon-fluorine stereocenter. Application of a new 1-naphthyllactic acid-based iodine(III)-catalyst allows the control of tertiary carbon-fluorine stereocenters with up to 96% ee. Density functional theory calculations are performed to investigate the details of the mechanism and the factors governing the stereoselectivity of the reaction.

SUBMITTER: Wang Q

PROVIDER: S-EPMC7735711 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization.

Wang Qiang Q Lübcke Marvin M Biosca Maria M Hedberg Martin M Eriksson Lars L Himo Fahmi F Szabó Kálmán J KJ

Journal of the American Chemical Society 20201116 47

1,1-Disubstituted styrenes with internal oxygen and nitrogen nucleophiles undergo oxidative fluorocyclization reactions with <i>in situ</i> generated chiral iodine(III)-catalysts. The resulting fluorinated tetrahydrofurans and pyrrolidines contain a tertiary carbon-fluorine stereocenter. Application of a new 1-naphthyllactic acid-based iodine(III)-catalyst allows the control of tertiary carbon-fluorine stereocenters with up to 96% ee. Density functional theory calculations are performed to inves ...[more]

PMID: 33191747

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