3-Carboxamide oxindoles as 1,3-C,N-bisnucleophiles for the highly diastereoselective synthesis of CF3-containing spiro-δ-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atom

被引：2
作者：
Zhao, Hongcai [1 ]
Zhang, Zhengbing [1 ]
Lu, Wenhua [1 ]
Han, Pan [1 ]
Wang, Wei [1 ,2 ]
Jing, Linhai [1 ]
机构：
[1] China West Normal Univ, Chem Synth & Pollut Control Key Lab Sichuan Prov, Nanchong 637002, Peoples R China
[2] Wuhan Inst Technol, Pharmaceut Res Inst, Wuhan 430205, Peoples R China
来源：
TETRAHEDRON LETTERS | 2021年 / 83卷
基金：
中国国家自然科学基金;
关键词：
3-Carboxamide oxindole; delta-Lactam; Spirooxindole; Trifluoromethyl; CATALYTIC ASYMMETRIC-SYNTHESIS; NATURAL-PRODUCTS; ONE-POT; ENANTIOSELECTIVE SYNTHESIS; TRIFLUOROMETHYL KETONES; 4+2 ANNULATION; ALDOL REACTION; SPIROOXINDOLES; CONSTRUCTION; FLUORINE;
D O I：
10.1016/j.tetlet.2021.153426
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient strategy has been established for the synthesis of delta-lactam fused oxindoles via the Michael/N-hemiketalization cascade reaction of 3-carboxamide oxindoles and alpha,beta-unsaturated trifluoromethyl ketones. A wide range of structurally novel CF3-containing spiro-delta-lactam oxindoles featuring acyl at the ortho-position of spiro carbon atoms were obtained in moderate to good yields with excellent diastereoselectivities under mild conditions. This work represents the first example of a systematic study of 3-carboxamide oxindoles as 1,3-C,N bisnucleophiles. (C) 2021 Elsevier Ltd. All rights reserved.
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页数：5
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