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

✍ Scribed by Katarzyna Glegoła; Sine A. Johannesen; Laura Thim; Catherine Goux-Henry; Troels Skrydstrup; Eric Framery

Book ID
104095817
Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
181 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

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A series of novel chiral phosphine-imine ligands have been prepared by a two-step transformation from chiral ␣-phenylethylamine. The resulting chiral ligands were found to be effective for the palladium-catalyzed asymmetric allylic alkylation of 1,3-diphenylprop-2-en-1-yl pivalate with dimethyl malo

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