Asymmetric synthesis of carboxylic acid derivatives having an all-carbon alpha-quaternary center through Cu-catalyzed 1,4-addition of dialkylzinc reagents to 2-aryl acetate derivatives.
The asymmetric synthesis of carboxylic acid derivatives having an all-carbon alpha-quaternary center has been achieved via copper-catalyzed 1,4-addition of dialkylzinc reagents to aryl acetate derivatives in the presence of phosphoramidite ligand. High isolated yields and enantioselectivities were obtained. It was demonstrated that the Meldrum's acid and ester moieties present on the all-carbon quaternary center allow for a wide variety of subsequent transformations, leading to the expedient preparation of succinimides, succinate esters and succinic acids, gamma-butyrolactones, and beta-amino acid derivatives.
Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1.
Ashraf
A
Wilsily
Eric
E
Fillion
D000085:Acetates / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D000085:Acetates; D000475:Alkenes; D000596:Amino Acids; D002264:Carboxylic Acids; D008024:Ligands; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D002244:Carbon; D003300:Copper; D015032:Zinc