Xie Lei, Zhao Chenyi, Wang Zhaoxue, Chen Zirui, Zhao Yingying, Liu Xinghan, Xu Xiangdong, Liu Wanxing, Li Xiaojing, Wu Lingang
School of Pharmaceutical Sciences, Liaocheng University, Liaocheng 252000, Shandong, P. R. China.
Liaocheng Key Laboratory of Quality Control and Pharmacodynamic Evaluation of Ganoderma Lucidum, Liaocheng 252000, Shandong, P. R. China.
J Org Chem. 2023 Nov 17;88(22):15805-15816. doi: 10.1021/acs.joc.3c01878. Epub 2023 Oct 31.
An EtN-catalyzed cascade [3 + 2]-annulation of β-oxo-acrylamides with cyclic -sulfonyl ketimines or sulfamate-derived imines is developed under mild reaction conditions, which provides a concise and efficient route to access valuable sultam- or sulfamidate-fused imidazolidinone derivatives in good to excellent yields (80-95% yields) with excellent diastereoselectivities (>20:1 drs). The current protocol features atom economy, a transition-metal-free process, and broad functional group tolerance. Moreover, the asymmetric variant of the [3 + 2]-cycloaddition reaction was achieved in the presence of diphenylethanediamine or quinine-based bifunctional squaramide organocatalysts and , giving the corresponding chiral polycyclic imidazolidinones in 68-90% yields with 25-94% ees and >20:1 drs in all cases.
开发了一种在温和反应条件下，由EtN催化的β-氧代丙烯酰胺与环状磺酰基酮亚胺或氨基磺酸酯衍生的亚胺的串联[3 + 2]环化反应，该反应提供了一条简洁高效的途径，能够以良好至优异的产率（80 - 95%的产率）获得具有优异非对映选择性（>20:1 dr）的有价值的磺内酰胺或氨基磺酸酯稠合咪唑啉酮衍生物。当前的方法具有原子经济性、无过渡金属过程以及广泛的官能团耐受性。此外，在二苯乙二胺或奎宁基双功能方酰胺有机催化剂存在下实现了[3 + 2]环加成反应的不对称变体，在所有情况下，均以68 - 90%的产率、25 - 94%的对映体过量和>20:1的非对映选择性得到相应的手性多环咪唑啉酮。
