This Letter describes the first application of activated 3-substituted isoindolinones in asymmetric synthesis of aza-tricyclic heterocycles, belonging to the class of pyrrolizidines. It was found that diphenylprolinol trimethylsilyl (TMS) ether was particularly effective, allowing the obtaining of adducts in good yields and up to 96% ee via iminium ion catalysis in the reaction of unsaturated aldehydes.
Organocatalytic asymmetric synthesis of highly functionalized pyrrolizidines via cascade Michael/hemi-aminalization reactions of isoindolinones
SCORZELLI, FRANCESCO;DI MOLA, ANTONIA;PALOMBI, Laura;MASSA, Antonio
2015-01-01
Abstract
This Letter describes the first application of activated 3-substituted isoindolinones in asymmetric synthesis of aza-tricyclic heterocycles, belonging to the class of pyrrolizidines. It was found that diphenylprolinol trimethylsilyl (TMS) ether was particularly effective, allowing the obtaining of adducts in good yields and up to 96% ee via iminium ion catalysis in the reaction of unsaturated aldehydes.File in questo prodotto:
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