期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 47, 页码 20048-20057出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c09323
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资金
- Knut och Alice Wallenbergs Foundation [2018.0066]
- Swedish Research Council [201704235]
- Stiftelsen Olle Engkvist Byggmastare [192-0484]
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.
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