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 / S. Duce; F. Pesciaioli; L. Gramigna; L. Bernardi; A. Mazzanti; A. Ricci; G. Bartoli; G. Bencivenni. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - STAMPA. - 353:(2011), pp. 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.
