| 立体选择性合成2-(a-噻吩甲酰基)-3-取代苯基-4-乙氧羰基-5-甲基-反式-2,3-二氢呋喃 |
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| 引用本文： | 姜海燕 曹卫国 张慧 孙汝淑 陈杰 邓红梅 邵敏 朱士正. 立体选择性合成2-(a-噻吩甲酰基)-3-取代苯基-4-乙氧羰基-5-甲基-反式-2,3-二氢呋喃[J]. 中国化学, 2008, 26(4): 736-740. DOI: 10.1002/cjoc.200890137 |
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| 作者姓名： | 姜海燕 曹卫国 张慧 孙汝淑 陈杰 邓红梅 邵敏 朱士正 |
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| 作者单位： | 上海大学化学系, 上海 200444, 中国 中国科学院上海有机化学研究所金属有机国家重点实验室, 上海 200032, 中国 上海大学分析测试中心上海 200444，中国 中国科学院上海有机化学研究所氟化学开放实验室, 上海 200032, 中国 |
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| 摘 要： | 溴化(a-噻吩甲酰基)甲基三苯鉮1与3-取代苯甲叉基-2,4-戊二酮 2以碳酸钾为碱，在苯中55℃条件下反应，可以较好的收率、高立体选择性地生成反-2-(a-噻吩甲酰基)-3-取代苯基-4-乙氧羰基-5-甲基-2,3-二氢呋喃3。产物结构均经波谱予以确定。本文还提出了生成产物的可能机理。
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| 关 键 词： | 立体选择性合成 胂叶立德 二氢呋呋喃衍生物 |
| 收稿时间： | 2007-06-05 |
| 修稿时间： | 2007-10-08 |
Stereoselective Synthesis of trans‐2‐Thien‐α‐oyl‐3‐ [(un)substituted phenyl]‐4‐acetyl‐5‐methyl‐2,3‐dihydrofurans |
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| Hai‐Yan JIANG,Wei‐Guo CAO,Hui ZHANG,Ru‐Shu SUN,Jie CHEN,Hong‐Mei DENG,Min SHAO,Shi‐Zheng ZHU. Stereoselective Synthesis of trans‐2‐Thien‐α‐oyl‐3‐ [(un)substituted phenyl]‐4‐acetyl‐5‐methyl‐2,3‐dihydrofurans[J]. Chinese Journal of Chemistry, 2008, 26(4): 736-740. DOI: 10.1002/cjoc.200890137 |
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| Authors: | Hai‐Yan JIANG Wei‐Guo CAO Hui ZHANG Ru‐Shu SUN Jie CHEN Hong‐Mei DENG Min SHAO Shi‐Zheng ZHU |
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| Affiliation: | 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. Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, China |
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| Abstract: | Trans‐2‐thien‐α‐oyl‐3‐[(un)substituted phenyl]‐4‐acetyl‐5‐methyl‐2,3‐dihydrofurans 3 were prepared in good yields with high stereoselectivity by the reaction of thien‐α‐oylmethyltriphenylarsonium bromide 1 with 3‐[(un)substituted benzylidene]‐2,4‐pentadione 2 in benzene in the presence of potassium carbonate at 55 °C. The structure of compound 3 was confirmed by IR, MS, 1H NMR, 1H‐1H COSY, microanalysis and single crystal X‐ray diffraction analysis. The possible reaction mechanism for the formation of products was also proposed. |
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| Keywords: | stereoselective synthesis arsonium ylide dihydrofuran derivative |
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