Uracil-Cu(<scp>i</scp>) catalyst: allylation of cyclopropanols with Morita–Baylis–Hillman alcohols under water-tolerant conditions
作者:Jingwei Hou、Xiaohong Li、Kaiyu Yan、Lei Zhang、Teck-Peng Loh、Peizhong Xie
DOI:10.1039/d3sc04890j
日期:——
a uracil-copper catalytic system was developed to promote ring-opening allylation of cyclopropanols with allylic alcohols under water-tolerant conditions. A new C–OH bond-breaking model can well resolve the trade-off between the need for acidic activators for C(allyl)–OH bond cleavage and the demand for strong basic conditions for generating homoenolates. Therefore, Morita–Baylis–Hillman alcohols,
受铜与 DNA 和 RNA 的高亲和力的启发,开发了尿嘧啶-铜催化系统,以促进环丙醇与烯丙醇在耐水条件下的开环烯丙基化。一种新的C-OH键断裂模型可以很好地解决C(烯丙基)-OH键断裂所需的酸性活化剂与生成同烯醇盐所需的强碱性条件之间的权衡。因此,Morita-Baylis-Hillman 醇,而不是它们的预活化版本,可以直接掺入与环丙醇的脱水交叉偶联中,产生水作为唯一的副产物。多种功能化的δ 、 ε-不饱和酮以良好到高的收率和高E-选择性获得。