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Synlett 1997; 1997(12): 1391-1392
DOI: 10.1055/s-1997-1045
DOI: 10.1055/s-1997-1045
letter
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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
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
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