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- β-carboline products (spiroindolinones) are the core of some newly discovered anti-malarial agents. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

An easy entry to optically active spiroindolinones: Chiral Brønsted acid-catalysed Pictet-Spengler reactions of isatins

Pesciaioli F.;
2011

Abstract

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- β-carboline products (spiroindolinones) are the core of some newly discovered anti-malarial agents. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11697/150174
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