Zhu Chi-Fan, Chen Ling-Qi, Hao Wen-Juan, Cui Chen-Chang, Tu Shu-Jiang, Jiang Bo
School of Chemistry & Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China.
Org Lett. 2021 Apr 2;23(7):2654-2658. doi: 10.1021/acs.orglett.1c00564. Epub 2021 Mar 17.
A new Lewis acid-catalyzed [2 + 2] cycloaddition/retroelectrocyclization (CA-RE)/1,6-addition relay of aurone-derived 1-azadienes and 1-alkynylnaphthalen-2-ols has been reported, leading to the regio- and diastereoselective synthesis of 1,2-dihydrobenzofuro[3,2-]pyridine with a chiral carbon center and an axial chirality in good yields. This protocol enables the C-C double-bond scission/recombination to rapidly construct aza-heterocyclic architectures and features 100% atom utilization, a wide substrate scope, good compatibility with substituents, and excellent diastereoselectivity.
据报道，一种新型的路易斯酸催化的金酮衍生的1-氮杂二烯与1-炔基萘-2-醇的[2 + 2]环加成/逆电环化（CA-RE）/1,6-加成接力反应，能够以良好的产率实现具有手性碳中心和轴手性的1,2-二氢苯并呋喃[3,2 -]吡啶的区域和非对映选择性合成。该方法能够实现碳 - 碳双键的断裂/重组，从而快速构建氮杂环结构，具有100%的原子利用率、广泛的底物范围、与取代基的良好兼容性以及出色的非对映选择性。
