Dancing on Ropes - Enantioselective Functionalization of Preformed Four-Membered Carbocycles
Dancing on Ropes - Enantioselective Functionalization of Preformed Four-Membered Carbocycles
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绳索上的舞蹈——预制四元碳环的对映选择性功能化
DOI：
10.1002/cjoc.202100879
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发表时间：
2022-03-14
影响因子：
5.4
通讯作者：
Lu, Ping
中科院分区：
文献类型：
--
作者：
Chen, Jun;Zhou, Qiang;Lu, Ping
环丁烷衍生物在有机合成和药物设计中被认为是有用的结构基序。随着光化学的复兴，利用[2 + 2]-环加成反应对映选择性合成环丁烷衍生物的研究受到了广泛的关注。另一方面，预形成的四元碳环的对映选择性官能化正在成为获得具有多种结构模式的手性环丁烷衍生物的重要补充方法。在此，我们总结了自2012年以来该领域的最新进展。为了避免由应变释放驱动的不期望的C-C键断裂，选择相容的方法进行对映选择性官能化并且同时保持完整的四元环骨架是至关重要的。通过计算的氢化反应谱，这是用来评估所指示的C-C键的应变能的指导下，一个清晰的画面开发的方法结合应变能和增强的反应活性的四元碳环的官能化。
Comprehensive Summary Cyclobutane derivatives have been recognized as useful structural motifs in organic synthesis and drug design. With the revival of photochemistry, the enantioselective synthesis of cyclobutane derivatives using [2 + 2]-cycloadditions has garnered numerous attentions. On the other hand, enantioselective functionalization of preformed four-membered carbocycles is emerging as an important complementary approach to access chiral cyclobutane derivatives with versatile structural patterns. Herein, we summarize recent advances in this field from 2012. To avoid undesired C-C bond cleavage driven by strain-releasing, it is crucial to choose compatible methods for enantioselective functionalization and meanwhile preserving intact four-membered ring skeleton. Guided by calculated hydrogenation enthalpies, which are used to evaluate the strain energy of indicated C-C bond, a clear picture of the developed methodologies on functionalization of four-membered carbocycles combining the strain energy and enhanced reactivity is presented.