Zhan Yizhou, Liu Tao, Ren Jun, Wang Zhongwen
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China.
Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, 94 Weijin Road, Tianjin, 300071, China.
Chemistry. 2017 Dec 19;23(71):17862-17866. doi: 10.1002/chem.201704695. Epub 2017 Nov 22.
A novel Lewis acid-catalyzed [3+2] intramolecular cross-cycloaddition (IMCC) between aziridine 2,2-diesters and conjugated dienes has been developed. This is the first regiospecific IMCC of intramolecular 1,3-dipolar cycloadditions of azomethine ylides with carbon=carbon double bonds, and supplies a general and efficient strategy for construction of structurally complex and diverse aza-[n.2.1] skeletons. The [3+2]IMCC could be carried out under mild conditions and in gram scale. More importantly, 3-alkyl-substituted aziridines were also successful. The excellent structural diversity, the facile operation and the versatile post-modifications will support the applications of the [3+2]IMCC in natural products synthesis and drugs discovery.
已开发出一种新型路易斯酸催化的氮丙啶2,2 - 二酯与共轭二烯之间的[3 + 2]分子内交叉环加成反应（IMCC）。这是甲亚胺叶立德与碳 - 碳双键进行分子内1,3 - 偶极环加成反应的首例区域特异性IMCC，为构建结构复杂多样的氮杂[n.2.1]骨架提供了一种通用且高效的策略。该[3 + 2]IMCC可在温和条件下以克级规模进行。更重要的是，3 - 烷基取代的氮丙啶也取得了成功。出色的结构多样性、简便的操作以及多样的后期修饰将支持[3 + 2]IMCC在天然产物合成和药物发现中的应用。
