Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 38, Pages 13573-13583Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908089
Keywords
asymmetric hydrogenation; enamides; P ligands; stereoelectronic effects; tofacitinib
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Funding
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- CAS [QYZDY-SSW-SLH029]
- NSFC [21725205, 21432007, 21572246, 21702223, STCSM-18520712200]
- K. C. Wong Education Foundation
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We herein report the development of a conformationally defined, electron-rich, C-2-symmetric, P-chiral bisphosphorus ligand, ArcPhos, by taking advantage of stereoelectronic effects in ligand design. With the Rh-ArcPhos catalyst, excellent enantioselectivities and unprecedentedly high turnovers (TON up to 10 000) were achieved in the asymmetric hydrogenation of aliphatic carbocyclic and heterocyclic tetrasubstituted enamides, to generate a series of chiral cis-2-alkyl-substituted carbocyclic and heterocyclic amine derivatives in excellent enantiomeric ratios. This method also enabled an efficient and practical synthesis of the Janus kinase inhibitor (R)-tofacitinib.
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