Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 15, Pages 6394-6408Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo301288w
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- DAAD
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A new, highly efficient, and atom-economic access to a series of functionalized 2,5-disubstituted oxazoles from propargylic amides is reported. A series of propargylic amides were transformed to the corresponding alkylideneoxazolines by a gold(I) catalyst. The next step was an autoxidation to hydroperoxides bearing the heteroaromatic oxazoles. Experiments addressing the reaction mechanism reveal a radical pathway for this autoxidation process. hydroperoxides could conveniently be converted to the corresponding alcohols by reduction with sodium borohydride.
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