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Paper | Special issue | Vol 82, No. 2, 2011, pp. 1327 - 1336
Published online: 1st December, 2010
DOI: 10.3987/COM-10-S(E)79
Efficient Phenolic Oxidations to Construct ortho-Spirolactone Structures Using Oxo-Bridged Hypervalent Iodine(III) Compound

Naoko Takenaga, Teruyoshi Uchiyama, Daishi Kato, Hiromichi Fujioka, Toshifumi Dohi, and Yasuyuki Kita*

*College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan

Abstract

The intramoleular ortho-spirocyclization of naphthols 1 bearing carboxylic acid moieties as internal nucleophiles using hypervalent iodine reagents is described. The use of the μ-oxo-bridged hypervalent iodine(III) compound is remarkably effective for this transformation, and spirolactones 2 were obtained in good to excellent yields using the μ-oxo-bis[trifluoroacetato- (phenyl)iodine] 4 [PhI(OCOCF3)O(OCOCF3)IPh].The intramoleular ortho-spirocyclization of naphthols 1 bearing carboxylic acid moieties as internal nucleophiles using hypervalent iodine reagents is described. The use of the μ-oxo-bridged hypervalent iodine(III) compound is remarkably effective for this transformation, and spirolactones 2 were obtained in good to excellent yields using the μ-oxo-bis[trifluoroacetato- (phenyl)iodine] 4 [PhI(OCOCF3)O(OCOCF3)IPh].

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