Synfacts 2006(8): 0813-0813  
DOI: 10.1055/s-2006-942020
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Regio- and Stereoselective Allylic Alkylations of Chelated Enolates

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
U. Kazmaier*, D. Stolz
Universität des Saarlandes, Saarbrücken, Germany
Further Information

Publication History

Publication Date:
21 July 2006 (online)

Significance

Here the authors report on rhodium-catalyzed allylic alkylation. Phosphates as leaving groups were shown to be superior compared to other leaving groups typically used in these types of reactions (i.e., acetate). Trimethyl and triethyl phosphite were shown to be the most effective ligands and trifluoroacetyl was the best protecting group for the chelated glycine enolate nucleophile.