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: coreychemistry.harvard.edu
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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