Journal
ORGANIC LETTERS
Volume 10, Issue 21, Pages 5039-5042Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol8022165
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- University of Washington
- American Chemical Society Petroleum Research Fund
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0747543] Funding Source: National Science Foundation
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A metal-free oxidative cyclization of ureas onto unactivated alkenes using iodosylbenzene and an acid promoter is described. The products isolated are predominantly bicyclic isoureas resulting from an intramolecular oxyamination reaction. The acid type and urea substitution have a strong effect on the product formed. A variety of substrates form the isourea with high diastereoselectivity via syn addition including di- and trisubstituted alkenes. Hydrolysis of the isourea gives access to new diastereomerically pure prolinol derivatives.
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