Synthesis of Bisspiro(oxindole)s by DMAP-Catalyzed [3+2] Annulation of Isatin-Derived Morita-Baylis-Hillman Carbonates

被引：4
作者：
Wang, Xiaohao [1 ]
Wei, Xingfu [1 ]
Xu, Yongqiang [1 ]
Qu, Jingping [1 ]
Wang, Baomin [1 ]
机构：
[1] Dalian Univ Technol, Sch Chem Engn, Dept Pharmaceut Engn, State Key Lab Fine Chem, 2 Linggong Rd, Dalian 116024, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 28期
关键词：
3+2] annulation; Lewis base catalysis; Morita-Baylis-Hillman carbonates; p-quinone methides; Spirooxindoles;
D O I：
10.1002/ejoc.202400396
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A straightforward [3+2] annulation method for synthesizing bisspiro(oxindole) derivatives has been developed by using isatin-derived Morita-Baylis-Hillman carbonates and p-quinone methides (p-QMs) with 4-dimethylaminopyridine (DMAP) as the catalyst. The optimized protocol in dichloromethane (DCM) solvent achieves good yields (up to 87 %) and diastereoselectivity (>20 : 1). The versatility of the method is shown through the synthesis of various derivatives, including chiral variants with up to 82 % ee. The intermediates were captured by HRMS, and a plausible reaction pathway was proposed.
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页数：5
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