4.7 Article

Bronsted Acid-Catalyzed Enantioselective Synthesis of IsatinDerived N,S-Acetals

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 357, Issue 4, Pages 672-676

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201401155

Keywords

N,S-acetals; asymmetric synthesis; organocatalysis; oxindoles; phosphoric acids

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The enantioselective organocatalytic nucleophilic addition of thiols to isatin-derived ketimines has been developed utilizing only 1 mol% of an enantiopure BINOL-derived phosphoric acid. The new protocol provides a series of isatin-derived N,S-acetals in high yields (up to 98%) and high enantioselectivities (up to 93% ee).

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