Xia Yong, Liu Xiaohua, Feng Xiaoming
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.
Angew Chem Int Ed Engl. 2021 Apr 19;60(17):9192-9204. doi: 10.1002/anie.202006736. Epub 2020 Dec 15.
Due to the synergistic "push-pull" effect of vicinal electron-donating and electron-withdrawing groups, donor-acceptor (D-A) cyclopropanes have been recognized as one of the most powerful building blocks to generate polyfunctional reactive intermediates after a strain-driven ring cleavage. Enantioselective reactions of D-A cyclopropanes provide an efficient approach to enantioenriched acyclic and cyclic compounds. A number of chiral Lewis/Brønsted acids, transition metals, and organocatalysts have been designed for such transformations, including ring-openings, annulations, and rearrangements. This minireview highlights the developments and new advances in this field and describes new synthetic opportunities offered by these interesting methodologies.
由于相邻给电子基团和吸电子基团的协同“推-拉”效应,供体-受体(D-A)环丙烷被认为是应变驱动开环后生成多官能团反应中间体的最强大的结构单元之一。D-A环丙烷的对映选择性反应为对映体富集的无环和环状化合物提供了一种有效方法。已经设计了许多手性路易斯/布朗斯特酸、过渡金属和有机催化剂用于此类转化,包括开环、环化和重排。本综述重点介绍了该领域的发展和新进展,并描述了这些有趣方法所提供的新合成机会。