Alkyl 4-Chlorobenzoyloxycarbamates as Highly Effective Nitrogen Source Reagents for the Base-Free, Intermolecular Aminohydroxylation Reaction

Ethyl- (7), benzyl- (8), tert-butyl- (9), and fluorenylmethyl-4-chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effectiv...

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Bibliographic Details
Published in:Journal of organic chemistry 2011-01, Vol.76 (2), p.358-372
Main Authors: Harris, Lawrence, Mee, Simon P. H, Furneaux, Richard H, Gainsford, Graeme J, Luxenburger, Andreas
Format: Article
Language:English
Subjects:
Alkanes - chemistry
Carbamates - chemistry
Catalysis
Chemistry
Chromatography, High Pressure Liquid
Exact sciences and technology
Hydroxylation
Indicators and Reagents - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Nitrogen - chemistry
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Stereoisomerism
Ultraviolet Rays
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Summary:Ethyl- (7), benzyl- (8), tert-butyl- (9), and fluorenylmethyl-4-chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo1018816