Selective Monoprotection of Symmetrical Diols in a Flow Reactor
Selective Monoprotection of Symmetrical Diols in a Flow Reactor作者机构:Department of Pharmaceutical Sciences Yokohama University of Pharmacy Yokohama Japan
出 版 物:《International Journal of Organic Chemistry》 (有机化学国际期刊(英文))
年 卷 期:2018年第8卷第2期
页 面:264-271页
主 题:Desymmetrization Selective Monoprotection Flow Synthesis Diols Tetrahydropyranylation
摘 要:Desymmetrization reactions provide a powerful approach for the construction of complex molecules. Various methods have been developed for the selective monoprotection of symmetrical diols;however, their application to large-scale operations is limited. In this study, the monotetrahydropyranylation of symmetrical diols in a flow reactor has been developed, whereby the length of the flow reactor tube and the amount of acid were optimized. A higher selectivity for the monoprotected derivative was observed when the reaction was performed in a flow reactor compared with that observed in a conventional batch experiment. The efficient flow method developed herein can be applied to large-scale synthesis by numbering up the flow reactor without affecting the selectivity and yield. Since monoprotection can be achieved without using a large excess of diol, our developed flow method is effective when expensive diol must be used.