The first catalytic asymmetric Pictet–Spengler reaction of isatins is presented. BINOLderived 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-b-carboline products (spiroindolinones) are the core of some newly discovered antimalarial agents.
An Easy Entry to Optically Active Spiroindolinones: Chiral Brønsted Acid-Catalysed Pictet–Spengler Reactions of Isatins
PESCIAIOLI, FABIO;GRAMIGNA, LUCIA;BERNARDI, LUCA;MAZZANTI, ANDREA;RICCI, ALFREDO MARCO;BARTOLI, GIUSEPPE;BENCIVENNI, GIORGIO
2011
Abstract
The first catalytic asymmetric Pictet–Spengler reaction of isatins is presented. BINOLderived 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-b-carboline products (spiroindolinones) are the core of some newly discovered antimalarial agents.File in questo prodotto:
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