Highly stereoselective synthesis of 1-cyanocyclopropane-carboxamides from 3-substituted-2-cyanoacrylamides with N-tosylhydrazones under metal-free conditions

被引：14
作者：
Nie, Xufeng [1 ]
Wang, Yachuan [1 ]
Yang, Lijun [1 ]
Yang, Zaijun [1 ]
Kang, Tairan [1 ,2 ]
机构：
[1] Collaborat Innovat Ctr Tissue Repair Mat Sichuan, Chem Synth & Pollut Control Key Lab, 1 Shida Rd, Nanchong 637000, Peoples R China
[2] West China Hosp, Canc Ctr, Collaborat Innovat Ctr Biotherapy, State Key Lab Biotherapy, 3 Peoples South Rd, Chengdu 610000, Peoples R China
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 31期
基金：
中国国家自然科学基金;
关键词：
N-Tosylhydrazones; 1-Cyanocyclopropane carboxamides; Electron-deficient olefins; Transition-metal-free; Diazomethane; CROSS-COUPLING REACTIONS; RHODIUM-CATALYZED CYCLOPROPANATION; ELECTRON-DEFICIENT ALKENES; H BOND FUNCTIONALIZATION; ASYMMETRIC CYCLOPROPANATION; DIASTEREOSELECTIVE SYNTHESIS; CHIRAL LIGANDS; ONE-POT; INTRAMOLECULAR CYCLOPROPANATION; CARBENE TRANSFORMATIONS;
D O I：
10.1016/j.tetlet.2017.05.070
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A metal-free cyclopropanation of electron-deficient olefins 3-substituted-2-cyanoacrylamides with N-tosylhydrazones has been successfully developed. This strategy provide a simple route to the synthesis of very valuable 1-cyanocyclopropanecarboxamides with a quaternary stereogenic center in good yields and with high diastereoselectivities (up to 90% yield with 19:1 dr). The reaction could be performed in one-pot fashion and in a gram-scale from aryl aldehydes. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3003 / 3007
页数：5
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