Lin Chen, Zhang Simiao, Wang Jingyi, Chen Lei, Zhu Yiwei, Du Ding
State Key Laboratory of Natural Medicines, School of Science, China Pharmaceutical University, Nanjing 210009, P.R. China.
School of Chemistry and Environmental Engineering, Anhui Polytechnic University, Wuhu, Anhui 241000, P.R. China.
Org Lett. 2022 May 27;24(20):3631-3635. doi: 10.1021/acs.orglett.2c01165. Epub 2022 May 12.
An unprecedented organocatalytic asymmetric construction of novel six-membered carbocycle fused uracils has been demonstrated by the reaction of the remotely enolizable 6-methyluracil-5-carbaldehydes with 2-bromoenals. The reaction involves an N-heterocyclic carbene-catalyzed formal [4 + 2] annulation of -quinodimethane (QDM) dienolates with α,β-unsaturated acylazoliums, followed by a cascade lactone formation/decarboxylation process. This protocol unlocks a new platform to access enantioenriched carbocycle-fused uracils.
通过可远程烯醇化的6-甲基尿嘧啶-5-甲醛与2-溴烯醛的反应，实现了新型六元碳环稠合尿嘧啶的前所未有的有机催化不对称构建。该反应涉及N-杂环卡宾催化的喹二甲基甲烷（QDM）烯醇化物与α,β-不饱和酰基唑鎓的形式[4 + 2]环化反应，随后是串联内酯形成/脱羧过程。该方案为获得对映体富集的碳环稠合尿嘧啶开辟了一个新平台。
