New insight into the mechanism of hypervalent iodine oxidation of flavanones

TitleNew insight into the mechanism of hypervalent iodine oxidation of flavanones
Publication TypeJournal Article
Year of Publication2002
AuthorsJuhász, L, Szilágyi, L, Antus, S, Visy, J, Zsila, F, Simonyi, M
JournalTetrahedron
Volume58
Issue21
Pagination4261 - 4265
Date Published2002
Keywords2,3-dihydrobenzo[b]furans, Flavanones, Hypervalent iodine, Stereospecific ring contraction
Abstract

Flavanone (1) on oxidation with iodobenzene diacetate (PIDA) in the presence of sulfuric acid in trimethyl orthoformate (TMOF) undergoes a stereospecific ring contraction by an aryl shift to result in trans methyl 2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylate (4a) as a major product. The mechanism of this transformation has been discussed on the basis of NMR, CD and chiral HPLC evidence. © 2002 Elsevier Science Ltd. All rights reserved.

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