Transition Metal-Free-Catalyzed Regioselective Reversal in the Cyclization of 2-Diazo-3,5-dioxo-6-ynoates/ynones/ynamide: Synthesis of Diazo γ-Pyrones and Diazo 3(2H)-Furanones

doi:10.6023/cjoc201712014

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (7): 1663-1672.DOI: 10.6023/cjoc201712014 Previous Articles Next Articles

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无过渡金属催化2-重氮-3,5-二氧代-6-炔酯/炔酮/炔酰胺的区域选择性逆转环化:重氮γ-吡喃酮和重氮3(2H)-呋喃酮衍生物的合成

陆声乐, 涂现侠, 刘为顺, 沈利亭, 毛善检, 邓桂胜

湖南师范大学化学生物学与中药分析教育部重点实验室长沙 410081;湖南师范大学有机功能分子组装与应用重点实验室长沙 410081

收稿日期:2017-12-07 修回日期:2018-03-06 发布日期:2018-04-12
通讯作者: 邓桂胜 E-mail:gsdeng@hunnu.edu.cn
基金资助:
国家自然科学基金（No.21372071）及湖南省自然科学基金（No.2016JJ2080）资助项目.

Transition Metal-Free-Catalyzed Regioselective Reversal in the Cyclization of 2-Diazo-3,5-dioxo-6-ynoates/ynones/ynamide: Synthesis of Diazo γ-Pyrones and Diazo 3(2H)-Furanones

Lu Shengle, Tu Xianxia, Liu Weishun, Shen Liting, Mao Shanjian, Deng Guisheng

Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Hunan Normal University, Changsha 410081;Key Laboratory of the Assembly and Application of Organic Functional Molecules, Hunan Normal University, Changsha 410081

Received:2017-12-07 Revised:2018-03-06 Published:2018-04-12
Contact: 10.6023/cjoc201712014 E-mail:gsdeng@hunnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21372071) and the Hunan Provincial Natural Science Foundation (No. 2016JJ2080).

For HSbF₆/EtOH system, diazo γ-pyrones were cleanly obtained starting from 2-diazo-3,5-dioxo-6-ynoates/ynones/ynamide at 80℃, whereas diazo 3(2H)-furanones were predominantly generated in HOAc-Et₃N-1,2-dichloroethane system at 25℃. These diazo compounds can undergo an efficient Rh(Ⅱ)-catalyzed intermolecular cyclopropanation with alkene.

Key words: diazo γ-pyrone, diazo 3(2H)-furanone, synthesis, cyclopropanation, regioselectivity

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Lu Shengle, Tu Xianxia, Liu Weishun, Shen Liting, Mao Shanjian, Deng Guisheng. Transition Metal-Free-Catalyzed Regioselective Reversal in the Cyclization of 2-Diazo-3,5-dioxo-6-ynoates/ynones/ynamide: Synthesis of Diazo γ-Pyrones and Diazo 3(2H)-Furanones[J]. Chin. J. Org. Chem., 2018, 38(7): 1663-1672.

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无过渡金属催化2-重氮-3,5-二氧代-6-炔酯/炔酮/炔酰胺的区域选择性逆转环化:重氮γ-吡喃酮和重氮3(2H)-呋喃酮衍生物的合成

Transition Metal-Free-Catalyzed Regioselective Reversal in the Cyclization of 2-Diazo-3,5-dioxo-6-ynoates/ynones/ynamide: Synthesis of Diazo γ-Pyrones and Diazo 3(2H)-Furanones

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