Organic Chemistry Portal

Abstracts

Search:

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)


see article for more reactions

Abstract

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.

see article for more examples



Key Words

α-azidoketones, organocatalysis


ID: J48-Y2019