Asymmetric hydrogenation of trifluoromethyl ketones: application in the synthesis of Odanacatib and LX-1031
Literature Information
Publication Date
2021-04-29
DOI
10.1039/D1QO00368B
Impact Factor
5.281
Authors
Tiao-Zhen Zhu, Pan-Lin Shao, Xumu Zhang
View Original
Abstract
Due to their stereoelectronic properties, trifluoromethyl (or perfluoroalkyl) ketones are challenging substrates in asymmetric (transfer) hydrogenation. We have developed iridium/f-amphol and iridium/f-ampha catalysis systems, which provide a highly efficient method for the synthesis of chiral secondary 2,2,2-trifluoroethanols in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). The practicability of this methodology was demonstrated through the facile preparation of the key intermediates of Odanacatib and LX-1301.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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1-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
CAS Number:
1020174-04-2
Molecular Formula:
C10H17BN2O2
3-(Methylamino)-1-phenyl-1-propanone hydrochloride (1:1)
CAS Number:
2538-50-3
Molecular Formula:
C10H14ClNO
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