Application of Allylzinc Reagents as Nucleophiles in Matteson Homologations

Abstract

Allylzinc reagents are versatile nucleophiles that can be used in Matteson homologations. The linear substitution products are formed almost exclusively, and excellent E selectivities are observed in reactions of reagents with sterically demanding or aryl substituents on the double bond. The allylated boronic esters obtained can be converted into trifluoroborates or subjected to further homologations. Ozonolysis of the double bond provides aldehydes or ketones, and therefore, allylzinc reagents are useful acetaldehyde or ketone enolate equivalents.