One-pot regioselective synthesis of chromanyl(phenyl)-lambda(3)-iodanes: tandem oxidative cyclization and lambda(3)-iodanation of 3-phenylpropanols

One-pot regioselective synthesis of chromanyl(phenyl)-lambda(3)-iodanes: tandem oxidative cyclization and lambda(3)-iodanation of 3-phenylpropanols

Reaction of 3-phenylpropanol with an activated iodosylbenzene-18-crown-6 complex [PhI(OH)BF4-18C6] in dichloromethane in the presence of BF3-Et2O afforded directly the 6-chromanyl(phenyl)-lambda3-iodane-18C6 complex through tandem oxidative intramolecular cyclization yielding chroman and its regiose...

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Veröffentlicht in:Organic letters 2007-05, Vol.9 (10), p.1995-1998
Hauptverfasser: Miyamoto, Kazunori, Hirobe, Masaya, Saito, Motomichi, Shiro, Motoo, Ochiai, Masahito
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
Cyclization
Iodine - chemistry
Models, Molecular
Molecular Structure
Oxidation-Reduction
Propanols - chemistry
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Zusammenfassung:Reaction of 3-phenylpropanol with an activated iodosylbenzene-18-crown-6 complex [PhI(OH)BF4-18C6] in dichloromethane in the presence of BF3-Et2O afforded directly the 6-chromanyl(phenyl)-lambda3-iodane-18C6 complex through tandem oxidative intramolecular cyclization yielding chroman and its regioselective phenyl-lambda3-iodanation.
ISSN:1523-7060
DOI:10.1021/ol0706105