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2005
Pyran derivatives
R 0340
Structure—Reactivity Relationships in Oxidative Carbon—Carbon Bond FormReactions: A Mild and Efficient Approach to Stereoselective Syntheses of
06- 131 ing
2,6-Disubstituted Tetrahydropyrones. — Homobenzylic ethers bearing enol acetate
nucleophiles are transformed into the title pyrones with excellent stereocontrol in the
presence of mild oxidant CAN. The cyclizations proceed via either stabilized or nonstabilized oxocarbenium ions. For ethers (VII) and (IX), the reaction conditions fail to
give the expected pyrones. In the case of ether (VII), a nucleophilic attack by nitrate on
the aromatic nucleus occurs, whereas in the case of ether (IX), the allylsilane bond is
cleaved followed by reaction with nitrate. — (WANG, L.; SEIDERS, J. R. I.;
FLOREANCIG*, P. E.; J. Am. Chem. Soc. 126 (2004) 39, 12596-12603; Dep.
Chem., Univ. Pittsburgh, Pittsburgh, PA 15260, USA; Eng.) — Klein
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