通过Morita-Baylis-Hillman碳酸酯与活化的邻乙烯基苯甲醛的顺序组装构建手性甲烷并苯并[7]环壬酮骨架。
Sequential Assembly of Morita-Baylis-Hillman Carbonates and Activated ortho-Vinylbenzaldehydes To Construct Chiral Methanobenzo[7]annulenone Frameworks.
作者信息
Jiang Bo, Xiao Ben-Xian, Ouyang Qin, Liang Hua-Ping, Du Wei, Chen Ying-Chun
机构信息
Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy , Sichuan University , Chengdu 610041 , China.
State Key Laboratory of Trauma, Burn and Combined Injury, and College of Pharmacy , Third Military Medical University , Shapingba, Chongqing 400038 , China.
出版信息
Org Lett. 2019 May 3;21(9):3310-3313. doi: 10.1021/acs.orglett.9b01058. Epub 2019 Apr 18.
The α-regioselective asymmetric [3 + 2] annulation reaction of Morita-Baylis-Hillman carbonates from isatins and activated ortho-vinylbenzaldehyses was developed by the catalysis of a chiral tertiary amine. The sequential N-heterocyclic carbene-mediated intramolecular Stetter reaction was conducted to finally furnish the bridged 5,8-methanobenzo[7]annulen-9-one architectures incorporating a spirooxindole motif with excellent stereoselectivity.
在手性叔胺催化下，实现了异吲哚酮与活化的邻乙烯基苯甲醛的Morita-Baylis-Hillman碳酸酯的α-区域选择性不对称[3+2]环化反应。接着进行了氮杂环卡宾介导的分子内Stetter反应，最终以优异的立体选择性构建了含有螺环氧化吲哚基序的桥连5,8-亚甲基苯并[7]环壬-9-酮结构。
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