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New chiral phosphinoimidazolidine ligand in palladium-catalyzed asymmetric allylic substitution

✍ Scribed by Myung-Jong Jin; Sang-Han Kim; Sang-Joon Lee; Young-Mok Kim

Book ID
104251970
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
116 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Chiral phosphinoimidazolidine 3 was used as an excellent ligand in Pd-catalyzed asymmetric allylic alkylation of racemic 1,3-diphenyl-2-propenyl acetate 5 with dimethyl malonate. Outstanding enantioselectivity of up to 99% and remarkable catalytic activity were observed. The ligand was also found to be effective in the asymmetric allylic amination of 5 with benzylamine.

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New chiral phosphinooxazolidines were prepared and examined as chiral ligands in Pd-catalyzed asymmetric allylic substitution reaction of 1,3-diphenyl-2propenyl acetate with dimethyl malonate or benzylamine. Enantioselectivity up to 9896 was observed.

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reactions of 1,3diphenyl-2-propenyl acetate (II). Best results are obtained with derivative (Ia). Dimethyl malonate as nucleophile gives the product (IV) with high e.e., whereas benzylamine provides only moderate stereoselectivity. -(JIN, MYUNG-