Liu Dan, Cao Jun, Sun Jing, Liu Ru-Zhang, Yan Chao-Guo
College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
Org Lett. 2020 Nov 20;22(22):8931-8936. doi: 10.1021/acs.orglett.0c03331. Epub 2020 Nov 9.
A triethylamine-promoted domino reaction of three molecular 1,3-indanediones with various 3-methyleneoxindoles in refluxing ethanol has been developed. Series of novel polycyclic triindanone-fused spiro[bicyclo[2.2.2]octane-2,3'-indoline] derivatives were successfully synthesized in satisfactory yields with high diastereoselectivity. This domino reaction was accomplished with in situ generation of active cyclic dienes by base-promoted cyclotrimerization or cyclotetramerization of 1,3-indanediones and sequential Diels-Alder reaction of active cyclic dienes with dienophilic 3-methyleneoxindoles.
已开发出一种三乙胺促进的三分子1,3-茚满二酮与各种3-亚甲基氧化吲哚在回流乙醇中的多米诺反应。一系列新型多环三茚满酮稠合的螺[双环[2.2.2]辛烷-2,3'-吲哚啉]衍生物以令人满意的产率和高非对映选择性成功合成。该多米诺反应是通过1,3-茚满二酮的碱促进环三聚或环四聚原位生成活性环状二烯，并使活性环状二烯与亲双烯体3-亚甲基氧化吲哚进行连续的狄尔斯-阿尔德反应来完成的。
