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.
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