School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata, 700032, India.
Angew Chem Int Ed Engl. 2021 Apr 12;60(16):8786-8791. doi: 10.1002/anie.202015004. Epub 2021 Mar 8.
Enantioenriched acyclic α-substituted β-hydroxy amides are valuable compounds in chemical, material and medicinal sciences, but their enantioselective synthesis remains challenging. A catalytic kinetic resolution (KR) of such amides with selectivity factor(s) up to >200 is developed via enantioselective acylation of primary alcohol with N-heterocyclic carbene. An enhanced selectivity for the catalytic KR process is realized using cyclic tertiary amine as base additive. Diastereomeric transition state models for the process are proposed to rationalize the origin of enantioselectivity.
对映富集的非环 α-取代的 β-羟基酰胺在化学、材料和医学科学中是很有价值的化合物，但它们的对映选择性合成仍然具有挑战性。通过 N-杂环卡宾对伯醇的对映选择性酰化反应，开发了对映选择性动力学拆分（KR）此类酰胺的方法，其选择性因子高达>200。使用环状叔胺作为碱添加剂，实现了对催化 KR 过程的增强选择性。提出了该过程的非对映过渡态模型，以合理化对映选择性的起源。
