4.8 Article

Palladium-Catalyzed Regio- and Enantioselective Hydrophosphination of gem-Difluoroallenes

Journal

ORGANIC LETTERS
Volume 25, Issue 32, Pages 5957-5962

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c02031

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In this study, a straightforward and efficient enantioselective hydrophosphination of gem-difluoroallenes using disubstituted phosphines was developed. A wide range of enantioenriched fluorinated allylic phosphines were successfully synthesized with excellent regio- and enantioselectivity, demonstrating their potential for synthetic and catalytic applications.
Chiral allylic phosphines and gem-difluoroalkenesare both important structural motifs in various bioactive molecules,chiral ligands, and natural products. These two motifs are now integrated,and we herein report a straightforward and atom-economical enantioselectivehydrophosphination of gem-difluoroallenes using disubstitutedphosphines. A wide array of enantioenriched fluorinated allylic phosphineshas been accessed with excellent regio- and enantioselectivity andhigh efficiency. Synthetic and catalytic applications of phosphineproducts have been demonstrated.

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