Ponra Sudipta, Yang Jianping, Kerdphon Sutthichat, Andersson Pher G
Department of Organic Chemistry, Stockholm University, Svante Arrhenius väg 16C, SE-10691, Stockholm, Sweden.
School of Chemistry and Physics, University of KwaZulu-Natal, Durban, South Africa.
Angew Chem Int Ed Engl. 2019 Jul 1;58(27):9282-9287. doi: 10.1002/anie.201903954. Epub 2019 May 17.
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.
开发用于合成手性含氟分子的新通用方法对多个科学学科都很重要。我们在此公开了一种基于铱催化的三取代烯基氟化物不对称氢化反应来制备手性有机氟分子的直接方法。这种催化不对称过程能够合成有或没有羰基取代的手性氟分子。由于氮杂双环噻唑 - 膦铱催化剂的空间和电子性质可调，这种立体选择性反应可以得到优化，并且发现它与具有各种官能团的各种芳香族、脂肪族和杂环体系兼容，能以优异的产率和对映选择性提供非常理想的产物。
