m -Chloroperbenzoic acid-oxchromium (VI)-mediated cleavage of 2,4,5-trisubstituted oxazoles

Content Provider	Scilit
Author	Patil, Pravin C. Luzzio, Frederick A.
Copyright Year	2017
Description	Journal: Tetrahedron Letters An array of 2-substituted-4,5-diphenyloxazoles were found to be cleaved to triacylamines and diacylamines (imides) using a reagent system composed of 3-chloroperbenzoic acid (MCPBA) and 2,2'-bipyridinium chlorochromate (BPCC). The 2-alkyl-4,5-diphenyloxazoles give imides (38-60%) as the predominant cleavage product while the 2-aryl-4,5-diphenyloxazoles give triacylamines (44-71%). Two mechanisms involving intermediates such as cyclic endoperoxides or oxachromacycles were proposed. An application of the oxidative cleavage to the multi-step synthesis of (±)-phoracantholide I seco acid is detailed.
Related Links	http://europepmc.org/articles/pmc5621761?pdf=render https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5621761/pdf
Ending Page	1282
Page Count	3
Starting Page	1280
ISSN	00404039
DOI	10.1016/j.tetlet.2017.02.027
Journal	Tetrahedron Letters
Issue Number	13
Volume Number	58
Language	English
Publisher	Elsevier BV
Publisher Date	2017-03-01
Access Restriction	Open
Subject Keyword	Journal: Tetrahedron Letters Organic Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Drug Discovery Biochemistry