期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 24, 页码 11283-11295出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo302393u
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资金
- National Science and Engineering Research Council (NSERC) of Canada
- Fonds Quebecois de Recherche-Nature et Technologies (FQRNT)
- Canada Foundation for Innovation (CFI)
- FQRNT Centre in Green Chemistry and Catalysis (CGCC)
- Universite de Sherbrooke
- Hydro-Quebec
A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated alpha-tosyloxylation of ketone derivatives. The alpha-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.
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