Asymmetric Synthesis of Alkyl Fluorides: Hydrogenation of Fluorinated Olefins,Angewandte Chemie International Edition

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Asymmetric Synthesis of Alkyl Fluorides: Hydrogenation of Fluorinated Olefins
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2019-05-17 , DOI: 10.1002/anie.201903954
Sudipta Ponra ₁ , Jianping Yang ₁ , Sutthichat Kerdphon ₁ , Pher G. Andersson _{1,

2}

Affiliation

The development of new general methods for the synthesis of chiral fluorine‐containing molecules is important for several scientific disciplines. We herein disclose a straightforward method for the preparation of chiral organofluorine molecules that is based on the iridium‐catalyzed asymmetric hydrogenation of trisubstituted alkenyl fluorides. This catalytic asymmetric process enables the synthesis of chiral fluorine molecules with or without carbonyl substitution. Owing to the tunable steric and electronic properties of the azabicyclo thiazole‐phosphine iridium catalyst, this stereoselective reaction could be optimized and was found to be compatible with various aromatic, aliphatic, and heterocyclic systems with a variety of functional groups, providing the highly desirable products in excellent yields and enantioselectivities.

中文翻译：

烷基氟化物的不对称合成：氟化烯烃的氢化

合成手性含氟分子的新通用方法的开发对于一些科学学科而言非常重要。我们在此公开了一种简单的制备手性有机氟分子的方法，该方法基于铱取代的三取代链烯基氟化物的铱催化不对称氢化。该催化不对称过程使得能够合成具有或不具有羰基取代的手性氟分子。由于氮杂双环噻唑-膦铱催化剂具有可调节的空间和电子特性，因此可以优化该立体选择性反应，发现该立体选择性反应可与具有各种官能团的各种芳族，脂族和杂环体系兼容，从而提供了非常理想的产品具有优异的收率和对映选择性。

更新日期：2019-05-17

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