Simple d-glucosamine-based phosphine-imine and phosphine-amine ligands in Pd-catalyzed asymmetric allylic alkylations

A new family of phosphine-imine and phosphine-amine ligands based on d-glucosamine were synthesized in order to probe previous asymmetric allylic alkylation results with those of disaccharide ligands of the same class. In most cases, good-to-excellent activities and enantioselectivies were observed...

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Bibliographic Details
Published in:Tetrahedron letters 2008-11, Vol.49 (47), p.6635-6638
Main Authors: Glegoła, Katarzyna, Johannesen, Sine A., Thim, Laura, Goux-Henry, Catherine, Skrydstrup, Troels, Framery, Eric
Format: Article
Language:English
Subjects:
Allylic alkylation
d-Glucosamine
Phosphine-amine
Phosphine-imine
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Summary:A new family of phosphine-imine and phosphine-amine ligands based on d-glucosamine were synthesized in order to probe previous asymmetric allylic alkylation results with those of disaccharide ligands of the same class. In most cases, good-to-excellent activities and enantioselectivies were observed with these ligands with ee’s reaching up to 87% in the Pd-catalyzed allylic alkylation reaction of racemic ( E)-1,3-diphenyl-2-propenyl acetate with dimethyl malonate as the nucleophile.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.09.039