Herein we describe the first asymmetric organocatalytic synthesis of 3-substituted isoindolinones in a convenient aldolcyclization- rearrangement tandem reaction of malonates with 2- 15 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.

The first organocatalytic asymmetric synthesis of 3-substituted isoindolinones

PALOMBI, Laura;MASSA, Antonio
2012

Abstract

Herein we describe the first asymmetric organocatalytic synthesis of 3-substituted isoindolinones in a convenient aldolcyclization- rearrangement tandem reaction of malonates with 2- 15 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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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11386/3308482
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