A three-component [3+2]-cycloaddition/elimination cascade for the synthesis of spirooxindole-pyrrolizines

被引：16
作者：
Palomba, Martina [1 ]
De Monte, Emanuela [1 ]
Mambrini, Andrea [1 ]
Bagnoli, Luana [1 ]
Santi, Claudio [1 ]
Marini, Francesca [1 ]
机构：
[1] Univ Perugia, Dept Pharmaceut Sci, Grp Catalysis Synth & Organ Green Chem, Via Liceo 1, I-06123 Perugia, Italy
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 03期
关键词：
MULTICOMPONENT 1,3-DIPOLAR CYCLOADDITION; ORGANOCATALYTIC MICHAEL ADDITION; ALPHA-AMINO-ACIDS; ONE-POT SYNTHESIS; AZOMETHINE YLIDES; VINYL SELENONE; COMBINATORIAL SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; REGIOSELECTIVE SYNTHESIS; HIGHLY EFFICIENT;
D O I：
10.1039/d0ob02321c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A three-component synthesis of novel spirooxindole-tetrahydropyrrolizines from secondary alpha-aminoacids, isatins and vinyl selenones has been disclosed. Products were formed in good yields and high diastereoselectivity by 1,3-dipolar cycloaddition of in situ generated azomethine ylides followed by spontaneous elimination of benzeneseleninic acid. Good regioselectivities with aryl substituted vinyl selenones were observed. The method showed good functional group tolerance, providing a direct approach to biologically relevant spirooxindoles under mild reaction conditions.
引用
收藏
页码：667 / 676
页数：10
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