|Title||New insight into the mechanism of hypervalent iodine oxidation of flavanones|
|Publication Type||Journal Article|
|Year of Publication||2002|
|Authors||Juhász, L, Szilágyi, L, Antus, S, Visy, J, Zsila, F, Simonyi, M|
|Pagination||4261 - 4265|
|Keywords||2,3-dihydrobenzo[b]furans, Flavanones, Hypervalent iodine, Stereospecific ring contraction|
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.