The first organocatalytic asymmetric synthesis of 3-substituted isoindolinones
2012
More, Vijaykumar | Rohlmann, Renate | Mancheño, Olga García | Petronzi, Carmen | Palombi, Laura | De Rosa, Antonio | Mola, Antonia Di | Massa, Antonio
Herein we describe the first asymmetric organocatalytic synthesis of 3-substituted isoindolinones in a convenient aldol-cyclization-rearrangement tandem reaction of malonates with 2-cyanobenzaldehyde. Bifunctional thiourea-cinchona catalysts proved to be particularly effective, giving the title compounds in high yields and moderate to good enantiomeric excesses. Moreover an efficient process of reverse crystallization led to a further enrichment up to >99% ee.
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