Dinuclear zinc catalyzed asymmetric [3+2] spiroannulation for the synthesis of diverse bispirocyclic saccharines

被引:17
作者
Chen, Shuang-Hu [1 ,2 ]
Miao, Yu-Hang [1 ,2 ]
Mei, Guang-Jian [1 ,2 ]
Hua, Yuan-Zhao [1 ,2 ]
Jia, Shi-Kun [1 ,2 ]
Wang, Min-Can [1 ,2 ]
机构
[1] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China
[2] Zhengzhou Univ, Inst Green Catalysis, Zhengzhou 450001, Peoples R China
基金
中国国家自然科学基金;
关键词
TRANS-PERHYDROINDOLIC ACID; ENANTIOSELECTIVE SYNTHESIS; CYCLIC; 1-AZADIENES; CONSTRUCTION; DERIVATIVES; CYCLOADDITIONS; ANNULATIONS; CARBONATES; OXINDOLES; ALDEHYDES;
D O I
10.1039/d2qo01039a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An atom-economical asymmetric [3 + 2] spiroannulation reaction of saccharine-derived cyclic 1-azadienes with alpha-hydroxy-1-indanones has been developed via bimetallic cooperative catalysis. The developed synthesis strategy achieved through the Michael/O-Mannich cascade process allows the highly enantioselective formation of novel and diverse bispirocyclic products, in which the biologically active indanone, tetrahydrofuran, and saccharine moieties are embedded. It is noteworthy that such a protocol represents the first example of the synthesis of bispirocyclic saccharines, which will provide some support for the enrichment of chiral heterocyclic compound databases with new bioactive molecules.
引用
收藏
页码:5010 / 5015
页数:6
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