| Highly Stereoselective Synthesis of trans-3-Aryl-4-carbethoxy-2,3-dihydro-2-fur-2＇-oyl-5-methylfurans |
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| 引用本文： | 张慧,曹卫国,陈杰,胡吉嵘,钱嘉贤,朱士正.Highly Stereoselective Synthesis of trans-3-Aryl-4-carbethoxy-2,3-dihydro-2-fur-2＇-oyl-5-methylfurans[J].中国化学,2007,25(7):968-972. |
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| 作者姓名： | 张慧 曹卫国 陈杰 胡吉嵘 钱嘉贤 朱士正 |
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| 作者单位： | [1]Department of Chemistry, Shanghai University, Shanghai 200444, China [2]State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China [3]Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China |
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| 基金项目： | Project supported by the National Natural Science Foundation of China （No. 20472047）, the Natural Science Foundation of Shanghai （No 04ZR14060） and the Education Commission of Shanghai Municipality （Nos. 05AX12 and B.99-0303-06-034）. |
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| 摘 要： | Multi-substituted dihydrofurans are valuable intermediates for the synthesis of natural products and pharmaceuticals. Considerable attention has been focused on the development of efficient and regioselective methods for their preparation. Using K2CO3 as a base, with the reaction of fur-2-oylmethyltriphenylarsonium bromide 1 and ethyl 2-acetyl-3-arylacrylate 2 in tetrahydrofuran at room temperature, we found an efficient protocol was achieved to synthesize trans-3-aryl-4-carbethoxy-2,3-dihydro-2-fur-2＇-oyl-5-methylfurans 3 in good yield with high stereoselectivity. The structure of compound 3 was confirmed by IR, ^1H NMR, MS and HRMS. The mechanism for the formation of 3 was proposed.
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| 关 键 词： | 选择性铅版合成 叶立德 氢化砷 二氢呋喃 |
| 修稿时间： | 2006-11-242007-03-16 |
Highly Stereoselective Synthesis of trans-3-Aryl-4-carbethoxy-2,3-dihydro-2-fur-2＇-oyl-5-methylfurans |
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| ZHANG Hui, CAO Wei-Guo,CHEN Jie, HU Ji-Rong, QIAN Jia-Xian,ZHU Shi-Zheng.Highly Stereoselective Synthesis of trans-3-Aryl-4-carbethoxy-2,3-dihydro-2-fur-2＇-oyl-5-methylfurans[J].Chinese Journal of Chemistry,2007,25(7):968-972. |
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| Authors: | ZHANG Hui CAO Wei-Guo CHEN Jie HU Ji-Rong QIAN Jia-Xian ZHU Shi-Zheng |
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| Institution: | 1. Department of Chemistry, Shanghai University, Shanghai 200444, China ;2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China ;3. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China |
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| Abstract: | Multi‐substituted dihydrofurans are valuable intermediates for the synthesis of natural products and pharmaceuticals. Considerable attention has been focused on the development of efficient and regioselective methods for their preparation. Using K2CO3 as a base, with the reaction of fur‐2‐oylmethyltriphenylarsonium bromide 1 and ethyl 2‐acetyl‐3‐arylacrylate 2 in tetrahydrofuran at room temperature, we found an efficient protocol was achieved to synthesize trans‐3‐aryl‐4‐carbethoxy‐2,3‐dihydro‐2‐fur‐2′‐oyl‐5‐methylfurans 3 in good yield with high stereoselectivity. The structure of compound 3 was confirmed by IR, 1H NMR, MS and HRMS. The mechanism for the formation of 3 was proposed. |
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| Keywords: | stereoselective synthesis arsonium ylide dihydrofuran derivative |
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