Han Man-Yi, Yang Fei-Yan, Zhou Di, Xu Zhigang
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui 235000, P.R. China.
Chongqing Key Laboratory for Advanced Materials and Technologies of Clean Energies, Faculty for Materials and Energy, Southwest University, Chongqing 400715, P.R. China.
Org Biomol Chem. 2017 Feb 7;15(6):1418-1425. doi: 10.1039/c7ob00005g.
A highly efficient [1,2]-Brook rearrangement of silyl glyoxylates has been developed using DBU as the organobase-catalyst. This [1,2]-Brook rearrangement is applicable to a number of thiols and secondary phosphine oxides containing acidic protons. These nucleophiles afford the corresponding Brook products in high yields. Using this methodology, a formal synthesis of anti-HIV drug compound lamivudine was realized.
以DBU作为有机碱催化剂，开发了一种高效的甲硅烷基乙醛酸酯的[1,2]-布鲁克重排反应。这种[1,2]-布鲁克重排反应适用于许多含有酸性质子的硫醇和二级氧化膦。这些亲核试剂能高产率地得到相应的布鲁克产物。利用该方法，实现了抗HIV药物化合物拉米夫定的形式合成。
