Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 6, Pages 860-864Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100050
Keywords
asymmetric catalysis; Bronsted acids; organocatalysis; Pictet-Spengler reaction; spirooxindoles
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Funding
- Stereoselezione in Chimica Organica, Metodologie e Applicazioni
- Universidad Autonoma de Madrid
- Comunidad Autonoma de Madrid
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The first catalytic asymmetric Pictet-Spengler reaction of isatins is presented. BINOL-derived phosphoric acids were found to be competent catalysts for this transformation, giving challenging spirooxindole structures bearing a quaternary stereocentre with generally good results. The 1,2,3,4-tetrahydro-beta-carboline products (spiroindolinones) are the core of some newly discovered antimalarial agents.
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