Cui Yanli, Mao Yangyi, Mao Jianwei, Zhang Yongmin
Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, UMR 8232 4 Place Jussieu 75005 Paris France
Department of Chemistry, Zhejiang University 38 Zheda Road Hangzhou 310027 China
RSC Adv. 2020 Mar 13;10(18):10695-10702. doi: 10.1039/d0ra00299b. eCollection 2020 Mar 11.
Following the trend of eco-friendly development, a smart regioselective modification is described herein, for mono 6-hydroxyl and penta-alkyl coexistence on the primary face of α-cyclodextrins with no additional catalysis or no enzyme process, just the adjustment of the ratio of alkali to alkylation agent, with good yields. The novel procedure minimized the tedious protection, deprotection steps and provided useful intermediates for further cutting edge research. Thus, the scope of green and economical access is extended from penta-pentenyl substitution to C-C alkyl group substitution. It was speculated that the mechanism might be controlled by the concentration of alkali in the system and the steric effects of the electrophilic reagent RBr.
顺应生态友好型发展趋势，本文描述了一种智能区域选择性修饰方法，用于在α-环糊精主面上实现单6-羟基和五烷基共存，无需额外催化或酶促过程，只需调节碱与烷基化剂的比例，即可获得良好产率。该新方法最大限度地减少了繁琐的保护、脱保护步骤，并为进一步的前沿研究提供了有用的中间体。因此，绿色经济合成的范围从五戊烯基取代扩展到碳-碳烷基取代。据推测，其机理可能受体系中碱的浓度和亲电试剂RBr的空间效应控制。
