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

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2019-12, Vol.141 (51), p.20058-20061
Main Authors: da Silva Gomes, Roberto, Corey, E. J
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b12315