Inside Cover: Design of Peptidyl Thiourea Derivatives as Organocatalysts for the Asymmetric Ring Opening ofmeso-Stilbene Oxides (Asian J. Org. Chem. 6/2014)

Abstract

Organocatalysis Organocatalytic asymmetric ring opening of epoxides with aliphatic amines has always been a challenge. In their Communication on page 700 ff., Swapandeep Singh Chimni report the design and synthesis of chiral peptidyl thiourea organocatalysts for the asymmetric ring opening of epoxides with N-phenylpiperazines. A tripeptide scaffold with a β-turn nucleating element provides favorable stereochemistry by positioning the nucleophile close to the epoxide. Chiral β-amino alcohols were obtained with up to 95% ee after crystallization. The configuration at the N-terminal residue of the catalyst affects the stereochemical outcome of the reaction.