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Synthesis of Chiral Α-Azido and Α-Amino Ketones From Racemic Α-Bromo Ketones,
Synthesis of Chiral Α-Azido and Α-Amino Ketones From Racemic Α-Bromo Ketones,
Racemic α-Bromo Ketones, and Its Generalization to the Formation of Bonds to C, O, and S
DOI: 10.1021/jacs.9b12315
Authors:
Roberto Gomes
Elias J. Corey
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Abstract
A new and practical method has been developed for the transformation of racemic α-bromo ketones to
chiral α-azido and α-amino ketones with high enantioselectivity using phase transfer, ion-pair mediated
reactions with a recoverable chiral quaternary salt (10 mol %) as catalyst in fluorobenzene-water. The
process has been generalized to a variety of other attachments including of C, O, S and NHR.