Diastereoselective Alkylation of Chiral 2‐Imidazolidinone Glycolates: Asymmetric Synthesis of α‐Hydroxy Carboxylic Acids.

Abstract

Enantioselective syntheses O 0031Diastereoselective Alkylation of Chiral 2-Imidazolidinone Glycolates: Asymmetric Synthesis of α-Hydroxy Carboxylic Acids. -Alkylation of sodium enolates derived from chiral 2-imidazolidinone glycolates (I) provides the corresponding α-alkylated products (III) in good yield and good to excellent diastereoselectivity. The imidazolidinone auxiliary can be easily removed by aqueous base without the need for peroxide furnishing the target α-hydroxy carboxylic acids (IV) in high yields. -(CHUN, C. C.; LEE, G.-J.; KIM, J. N.; KIM*, T. H.; Tetrahedron: Asymmetry 16