Highly stereoselective organocatalytic synthesis of pyrrolidinyl spirooxindoles containing halogenated contiguous quaternary carbon stereocenters

被引：18
作者：
Chen, Fei-Yu [1 ]
Xiang, Li [1 ]
Zhan, Gu [1 ]
Liu, Hong [1 ]
Kang, Bin [1 ]
Zhang, Shu-Cang [1 ]
Peng, Cheng [1 ]
Han, Bo [1 ]
机构：
[1] Chengdu Univ Tradit Chinese Med, Hosp Chengdu Univ Tradit Chinese Med, Sch Pharm, State Key Lab Southwestern Chinese Med Resources, Chengdu 611137, Peoples R China
来源：
TETRAHEDRON LETTERS | 2020年 / 61卷 / 17期
基金：
中国国家自然科学基金;
关键词：
Asymmetric organocatalytic synthesis; Contiguous quaternary carbons; Halogenated quaternary carbon; Spirooxindole; Covalent inhibitor; ASYMMETRIC 3+2 CYCLOADDITION; N-2,2,2-TRIFLUOROETHYLISATIN KETIMINES; ENANTIOSELECTIVE SYNTHESIS; IN-VIVO; 1,3-DIPOLAR CYCLOADDITION; COVALENT INHIBITORS; NATURAL-PRODUCTS; ALPHA; CONSTRUCTION; METABOLISM;
D O I：
10.1016/j.tetlet.2020.151806
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The highly stereoselective synthesis of pyrrolidine-fused spirooxindole derivatives bearing a carbon-halogen bond and contiguous quaternary carbon stereocenters was achieved via a [3 + 2] cycloaddition reaction. This method provided facile access to a collection of enantiomerically pure spiro[pyrrolidin-3,2'-oxindoles] containing halogenated contiguous quaternary carbon stereocenters in good to high yields (48-84%) and excellent stereoselectivity (up to >20:1 dr and >99% ee). The halogen-containing products can be stereoselectively transformed into sulfurated derivatives via nucleophilic substitution (S(N)2) reactions, indicating that they may serve as candidates in the development of covalent inhibitors with potential biological activity. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：7
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