Journal
ORGANIC LETTERS
Volume 16, Issue 1, Pages 58-61Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol403016p
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Funding
- grant agency of the Czech Republic [13-40188S]
- Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic [RVO: 61388963]
- Gilead Sciences & IOCB research center
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A new method for alcohol oxidation using TEMPO or AZADO in conjunction with BF3 center dot OEt2 or LiBF4 as precatalysts and tert-butyl nitrite as a stoichiometric oxidant has been developed. The system is based on a NO+/NO center dot pair for nitroxide reoxidation under anaerobic conditions. This allows the simple, high-yielding conversion of various achiral and chiral alcohols to carbonyl compounds without epimerization and no formation of nonvolatile byproducts.
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