期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 17, 页码 7755-7760出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo3013226
关键词
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资金
- National Institutes of Health [GM 078383]
Isoxazolidines are useful in organic synthesis, drug discovery, and chemical biology endeavors. A new stereoselective synthesis of methyleneoxy-substituted isoxazolidines is disclosed. The method involves copper-catalyzed aminooxygenation/cyclization of N-sulfonyl-O-butenyl hydroxylamines in the presence of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl radical (TEMPO) and O-2 and provides substituted isoxazolidines in excellent yields and diastereoselectivities. We also demonstrate selective mono N-O reduction followed by oxidation of the remaining N-O bond to reveal a 2-amino-gamma-lactone. Reduction of the gamma-lactone reveals the corresponding aminodiol.
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