@article{3b96b932838b4f039c629950f4f422f6,
title = "Formation of an endoperoxide upon chromium-catalyzed allylic oxidation of a triterpene by oxygen",
abstract = "The chromium-catalyzed allylic oxidation of triterpene 1 with O2 and N-hydroxyphthalimide (NHPI, 5 equiv) formed endoperoxide 2 in 76% yield at ambient temperature. Unlike standard allylic oxidations, this oxidation is catalytic in chromium because oxygen, not the chromium reagent, is the oxidant. This oxidation is sensitive to the precise structure of the substrate. The endoperoxide is only formed if ring A is unsaturated and ring C contains an enone. A mechanism is proposed that involves the coupling of two stabilized radicals on rings A and C to form endoperoxide 2.",
author = "Abbie Chung and Miner, {Matthew R.} and Richert, {Kathleen J.} and Rieder, {Curtis J.} and Woerpel, {K. A.}",
note = "Funding Information: This research was supported by the National Science Foundation (CHE-0848121) and is based on work supported for K.J.R. by the National Science Foundation Graduate Research Fellowship under Grant No. DGE-1342536 and a Sokol Fellowship from the NYU Department of Chemistry. M.R.M. was supported by a Margaret Strauss Kramer Fellowship from the NYU Department of Chemistry. We thank Dr. Chin Lin (NYU) for assistance with NMR spectroscopy and mass spectrometry. We also thank the Molecular Design Institute of NYU for purchasing a single-crystal diffractometer, and Dr. Chunhua Hu (NYU) for his assistance with data collection and structure determination. Funding Information: This research was supported by the National Science Foundation (CHE-0848121) and is based on work supported for K.J.R. by the National Science Foundation Graduate Research Fellowship under Grant No. DGE-1342536 and a Sokol Fellowship from the NYU Department of Chemistry. M.R.M. was supported by a Margaret Strauss Kramer Fellowship from the NYU Department of Chemistry. We thank Dr. Chin Lin (NYU) for assistance with NMR spectroscopy and mass spectrometry. We also thank the Molecular Design Institute of NYU for purchasing a singlecrystal diffractometer, and Dr. Chunhua Hu (NYU) for his assistance with data collection and structure determination. Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",
year = "2015",
month = jan,
day = "2",
doi = "10.1021/jo502344x",
language = "English (US)",
volume = "80",
pages = "266--273",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "1",
}