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Wiley, Advanced Synthesis & Catalysis, 14(348), p. 1883-1893, 2006

DOI: 10.1002/adsc.200606109

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Highly Diastereoselective Synthesis of 2,6-Di[1-(2-alkylaziridin-1-yl)alkyl]pyridines, Useful Ligands in Palladium-Catalyzed Asymmetric Allylic Alkylation

This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

C-2-Symmetrical, enantiopure 2,6-di[1-(1-aziridinyl)alkyl]pyridines (DIAZAPs) 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