C2-symmetric enantiopure 2,6-di[1-(1-aziridinyl)alkyl]pyridines (DIAZAP’s) were prepared by a high yielding three step sequence starting from 2,6-pyridinedicarbaldehyde and (S)-valinol or (S)-phenylglycinol. The new compounds were tested as ligands in palladium-catalyzed allylation of carbanions in different solvents. Almost quantitative yield and up to 99% enantiomeric excess were obtained in the reactions of the enolates derived from malonate, phenyl- and benzylmalonate dimethyl esters with 1,3-diphenyl-2-propenyl ethyl carbonate.
Highly diastereoselective synthesis of 2,6-di[1-(2-akylaziridin-1-yl)alkyl]pyridines, useful ligands in palladium-catalyzed asymmetric allylic alkylation / D. Savoia; G. Alvaro; R. Di Fabio; C. Fiorelli; A: Gualandi; M. Monari; F. Piccinelli. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - STAMPA. - 348:(2006), pp. 1883-1893. [10.1002/adsc.200606109]
Highly diastereoselective synthesis of 2,6-di[1-(2-akylaziridin-1-yl)alkyl]pyridines, useful ligands in palladium-catalyzed asymmetric allylic alkylation
SAVOIA, DIEGO;GUALANDI, ANDREA;MONARI, MAGDA;
2006
Abstract
C2-symmetric enantiopure 2,6-di[1-(1-aziridinyl)alkyl]pyridines (DIAZAP’s) were prepared by a high yielding three step sequence starting from 2,6-pyridinedicarbaldehyde and (S)-valinol or (S)-phenylglycinol. The new compounds were tested as ligands in palladium-catalyzed allylation of carbanions in different solvents. Almost quantitative yield and up to 99% enantiomeric excess were obtained in the reactions of the enolates derived from malonate, phenyl- and benzylmalonate dimethyl esters with 1,3-diphenyl-2-propenyl ethyl carbonate.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.