Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Rd., Shanghai, 200062, China.
Chem Commun (Camb). 2018 Nov 6;54(89):12650-12653. doi: 10.1039/c8cc06390g.
A highly diastereoselective approach for the rapid construction of an isochroman skeleton was achieved by the copper(ii)-catalyzed transformation of alcohol-tethered enones and diazo compounds. This transformation was proposed to proceed through the intramolecular Michael-type trapping of an in situ generated oxonium ylide intermediate. The copper(ii) catalyst may play a dual role in catalyzing diazo decomposition as well as activating the enone unit. With this method, a series of 3,4-substituted isochromans were obtained with excellent diastereoselectivities under very mild reaction conditions.
通过铜（II）催化醇键烯酮和重氮化合物的转化，实现了高度非对映选择性的快速构建异苯并呋喃骨架的方法。该转化被认为是通过原位生成的氧鎓叶立德中间体的分子内迈克尔型捕获进行的。铜（II）催化剂可能在催化重氮分解以及激活烯酮单元方面发挥双重作用。使用这种方法，在非常温和的反应条件下，一系列 3,4-取代的异苯并呋喃可以以优异的非对映选择性获得。
