Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization,Journal of the American Chemical Society

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Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-11-16 , DOI: 10.1021/jacs.0c09323
Qiang Wang ₁ , Marvin Lübcke ₁ , Maria Biosca ₁ , Martin Hedberg ₁ , Lars Eriksson ₂ , Fahmi Himo ₁ , Kálmán J. Szabó ₁

Affiliation

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.

中文翻译：

有机催化氟环化对三氟立体中心的对映选择性构建

具有内部氧和氮亲核试剂的 1,1-二取代苯乙烯与原位生成的手性碘 (III) 催化剂发生氧化氟环化反应。所得氟化四氢呋喃和吡咯烷含有叔碳氟立体中心。新型 1-萘基乳酸基碘 (III) 催化剂的应用可以控制高达 96% ee 的叔碳氟立体中心。进行密度泛函理论计算以研究机制的细节和控制反应立体选择性的因素。

更新日期：2020-11-16

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