Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 29, Pages 4891-4899Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200800656
Keywords
Alkynes; Furans; Gold; Isoindoles; Sulfoxides; Sulfones
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Furfurals and enantomerically pure sulfinamides have been condensed to N-sulfinylimines. Addition of organolithium or -magnesium compounds to these imines allowed a 1,2-induction. After propargylation, the sulfinamides gave low conversion with gold catalysts. Oxidation to chiral sulfonamides, propargylation and gold-catalysed cycloisomeriza- tion to the phenol delivered non-racemic dihydroisoindol-4ols in good yields. In situ NMR studies prove the intermediacy of the arene oxide even with the AuCl3 catalyst. ((C)Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
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