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Synlett 1997; 1997(12): 1391-1392
DOI: 10.1055/s-1997-1045
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Unexpected Stereoselective 6-exo versus 7-endo Aryl Radical Cyclisation Controlled by Positional Isomers in a Chiral Octahydro-1,3-benzoxazine Moiety

Celia Andrés, Juan P. Duque-Soladana, Jesús M. Iglesias1 , Rafael Pedrosa2
  • 1Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, 47011-Valladolid, Spain, Fax (83)-423013, e-mail: iglesias@cpd.uva.es
  • 2Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, 47011-Valladolid, Spain, Fax (83)-423013
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Publication History

Publication Date:
31 December 2000 (online)

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Chiral perhydro-1,3-benzoxazines which carry both olefinic and bromo-aromatic substituents undergo stereo- and regio-radical cyclisations mediated by Bu3SnH. Diastereomeric six-membered and seven-membered rings are formed in positional isomers through selective 6-exo and 7-endo attack respectively.

radical cyclisation - aryl radicals - perhydrobenzoxazine auxiliary - tetrahydroisoquinolines - tetrahydro-2-benzazepines

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