Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, United States.
J Org Chem. 2020 Nov 6;85(21):13391-13414. doi: 10.1021/acs.joc.0c01691. Epub 2020 Oct 20.
Due to their inherent ring strain and electrophilicity, epoxides are highly attractive building blocks for fundamental organic reactions. However, controlling the regioselectivity of disubstituted epoxide transformations is often particularly challenging. Most Lewis acid-mediated processes take advantage of intrinsic steric or electronic substrate bias to influence the site of nucleophilic attack. Therefore, the scope of many of these systems is frequently quite limited. Recent efforts to generate catalysts that can overcome substrate bias have expanded the synthetic utility of these well-known reactions. In this Perspective, we highlight various regioselective transformations of disubstituted epoxides, emphasizing those that have inspired the production of challenging, catalyst-controlled processes.
由于其固有环应变和亲电性，环氧化物是基础有机反应中极具吸引力的构建块。然而，控制二取代环氧化物转化的区域选择性通常特别具有挑战性。大多数路易斯酸介导的过程利用固有空间位阻或电子底物偏置来影响亲核进攻的位置。因此，这些系统的许多范围通常非常有限。最近努力开发可以克服底物偏置的催化剂，扩大了这些知名反应的合成实用性。在本观点中，我们强调了二取代环氧化物的各种区域选择性转化，重点介绍了那些激发了具有挑战性的、催化剂控制过程的转化。
