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.
S. Duce, F. Pesciaioli, L. Gramigna, L. Bernardi, A. Mazzanti, A. Ricci, et al. (2011). An Easy Entry to Optically Active Spiroindolinones: Chiral Brønsted Acid-Catalysed Pictet–Spengler Reactions of Isatins. ADVANCED SYNTHESIS & CATALYSIS, 353, 860-864 [10.1002/adsc.201100050].
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.