| Title | Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction |
| Publication Type | Journal Article |
| Year of Publication | 2011 |
| Authors | Harris, L., Mee S. P. H., Furneaux R. H., Gainsford G. J., and Luxenburger A. |
| IRL Team | Carbohydrate Chemistry |
| Journal | Journal of Organic Chemistry |
| Volume | 76 |
| Pagination | 358-372 |
| Keywords | benzyl 2 hydroxy 1 phenylethylcarbamate, benzyl 2 hydroxy 2 phenylethylcarbamate, benzyl 2 hydroxy 3 phenylpropylcarbamate, benzyl 2 hydroxycyclohexylcarbamate, benzyl 3 (benzyloxycarbonylamino) 4 hydroxypyrrolidine 1 carboxylate, benzyl 4 chlorobenzoyloxycarbamate, benzyl hydroxycarbamate, carbamic acid, chemical reaction, Cinnamates, dimethyl 2 (benzyloxycarbonylamino) 3 hydroxysuccinate, ethyl 4 chlorobenzoyloxycarbamate, ethyl hydroxycarbamate, Hydroxylation, isopropyl 2 (benzyloxycarbonylamino) 3 hydroxy 3 phenylpropanoate, isopropyl 3 (ethoxycarbonylamino) 2 hydroxy 3 phenylpropanoate, isopropyl 3 (tert butoxycarbonylamino) 2 hydroxy 3 phenylpropanoate, isopropyl 3 [[(9h fluoren 9 yl)methoxy]carbonylamino] 2 hydroxy 3 phenylpropanoate, methyl 3 (ethoxycarbonylamino) 2 hydroxy 3 phenylpropanoate, nitrogen, Nitrogen sources, Olefins, Reaction conditions, synthesis, tert butyl 4 chlorobenzoyloxycarbamate, tert butyl hydroxycarbamate, unclassified drug |
| 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. © 2010 American Chemical Society. |
| URL | http://www.scopus.com/inward/record.url?eid=2-s2.0-78651515922&partnerID=40&md5=8bf878cd444417714c2780fdceaa6401 |
| DOI | 10.1021/jo1018816 |
