Organocatalytic Enantioselective Peroxidation of Ketimines Derived from Isatins

The first catalytic enantioselective addition of hydroperoxides to ketimines derived from isatins has been developed. Excellent yields and enantioselectivities were observed for the reaction of various ketimines with peroxides using a cinchona alkaloid sulfonamide catalyst. Both enantiomers of produ...

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Bibliographic Details
Published in:Organic letters 2015-06, Vol.17 (11), p.2590-2593
Main Authors: Nakamura, Shuichi, Takahashi, Shun
Format: Article
Language:English
Subjects:
Catalysis
Cinchona Alkaloids - chemistry
Hydrogen Peroxide - chemistry
Imines - chemistry
Isatin - chemistry
Molecular Structure
Nitriles - chemistry
Peroxides - chemical synthesis
Peroxides - chemistry
Stereoisomerism
Sulfonamides - chemistry
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Summary:The first catalytic enantioselective addition of hydroperoxides to ketimines derived from isatins has been developed. Excellent yields and enantioselectivities were observed for the reaction of various ketimines with peroxides using a cinchona alkaloid sulfonamide catalyst. Both enantiomers of products could be obtained by using pseudoenantiomeric chiral catalysts. The obtained product can be converted to optically active α-amino hydroperoxide.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00805