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A Method for the Catalytic Enantioselective Synthesis of Chiral α-Azido and α-Amino Ketones from Racemic α-Bromo Ketones, and Its Generalization to the Formation of Bonds to C, O, and S

Roberto da Silva Gomes and E. J. Corey*

*Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States, Email:

R. da Silva Gomes, E. J. Corey, J. Am. Chem. Soc., 2019, 141, 20058-20061.

DOI: 10.1021/jacs.9b12315 (free Supporting Information)

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A recoverable chiral quaternary salt as catalyst enables phase transfer, ion-pair mediated reactions of racemic α-bromo ketones to chiral α-azido and α-amino ketones with high enantioselectivity in fluorobenzene-water. The process has been generalized to various other replacements of bromine.

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Key Words

α-azidoketones, organocatalysis

ID: J48-Y2019