ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Ligand Effect on Pd(0)-Catalyzed Allylation of Alkyl (Diphenylmethylene)glycinates

S. Gosiewska, B. Gotov, and Š. Toma

Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, SK-842 15 Bratislava

E-mail: toma@fns.uniba.sk

Received: 27 August 2002

Abstract: The effect of six different P,N-ferrocenyl ligands having both central and planar chirality on the stereoselectivity of Pd(0)-catalyzed allylation of methyl or (1R,2S,5R)-(-)-menthyl (diphenylmethylene) glycinate was studied. Just moderate yields of the allylation products were isolated. The highest stereoselectivity was achieved with the ligand (R,pS)-BPPFA, namely 25.5 % ee at allylation of methyl glycinate. It was proved that in allylation of (1R,2S,5R)-(-)-menthyl (diphenylmethylene) glycinate the ester chiral auxiliary has a dominant effect.

Full paper in Portable Document Format: 582a113.pdf

Chemical Papers 58 (2) 113–116 (2004)