Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 27, Pages 9282-9287Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201903954
Keywords
alkenyl fluorides; asymmetric hydrogenation; iridium catalysis; N,P ligands; organofluorine compounds
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Funding
- Swedish Research Council (VR)
- Stiftelsen Olle Engkvist Byggmastare
- Knut and Alice Wallenberg foundation [KAW 2016.0072, KAW 2018: 0066]
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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.
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