Gold Catalysis and Chiral Sulfoxides: Enantioselective Synthesis of Dihydroisoindol‐4‐ols

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 cycloisomerization to the phenol delivered non‐racemic dihydroisoindol‐4‐ols in good yields. In situ NMR studies prove the intermediacy of the arene oxide even with the AuCl3 catalyst.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)