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Tandem Wagner-Meerwein rearrangement-carbocation trapping in the formation of chiral heterocyclic ring systems

✍ Scribed by Scott M. Starling; Simone C. Vonwiller

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 231 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00271-2

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✦ Synopsis

Ortho fithiated protected anilines and phenols undergo exclusive addition to fenchone from the exo face. The corresponding adducts, under acidic conditions undergo cationic rearrangement followed by internal trapping of the new cation with amino, hydroxyl or methoxyl substitueats to give enantiomefically pure chiml heterocyclic ring systems. The nature of the rearrangexaent is dependent on the donor group and its ability to stabillse a positive charge. With an amino donor group a product due to Wagner-Meerwein rearrangement is formed while with a methoxy donor group Nametldn rearrangement is the preferred pathway.

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