title: Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction.
abstract: 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.
authors.affiliation: Carbohydrate Chemistry, Industrial Research Limited, P.O. Box 31-310, Lower Hutt, New Zealand.
authors.forename: Lawrence
authors.initials: L
authors.lastname: Harris
authors.forename: Simon P H
authors.initials: SP
authors.lastname: Mee
authors.forename: Richard H
authors.initials: RH
authors.lastname: Furneaux
authors.forename: Graeme J
authors.initials: GJ
authors.lastname: Gainsford
authors.forename: Andreas
authors.initials: A
authors.lastname: Luxenburger
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D006900:Hydroxylation; D007202:Indicators and Reagents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism; D014466:Ultraviolet Rays
chemical_list: D000473:Alkanes; D002219:Carbamates; D007202:Indicators and Reagents; D009584:Nitrogen