Lu Jian-Bin, Shi Chong-Hui, Hu Di, Gao Xin-Yue, Chen Zhi-Chao, Du Wei, Chen Ying-Chun
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.
College of Pharmacy, Third Military Medical University, Shapingba, Chongqing 400038, China.
Org Lett. 2021 Jan 1;23(1):145-149. doi: 10.1021/acs.orglett.0c03862. Epub 2020 Dec 16.
The cinnamates having an -formyl group can potentially form vinylogous iminium ion species under the catalysis of chiral amines, which facilitates the Diels-Alder cycloaddition reaction with the concurrently generated trienamines between dienals and amine catalysts in a regioselectivity umpolung manner. A cascade intramolecular aldol reaction was followed, finally furnishing polyhydrophenanthrene frameworks with excellent diastereo- and enantioselectivity.
具有甲酰基的肉桂酸酯在手性胺的催化下有可能形成连烯亚胺离子物种，这以区域选择性极性反转的方式促进了与同时生成的二烯醛和胺催化剂之间的烯胺的狄尔斯-阿尔德环加成反应。随后进行串联分子内羟醛反应，最终得到具有优异非对映选择性和对映选择性的多氢菲骨架。
