| Highly Stereoselective Synthesis of Phenylseleno- and p-Tolylsulfonyl Substituted 1,3-Dienes from Functionalized Allyl Alcohols |
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| 作者姓名： | 谢美华 黄宪 |
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| 作者单位： | Department of Chemistry，Zhejiang University (Xixi Campus)，Hangzhou，Zhejiang 310028，China Department of Chemistry，Anhui Normal University，Wuhu，Anhui 241000，China，Department of Chemistry，Zhejiang University (Xixi Campus)，Hangzhou，Zhejiang 310028，ChinaState Key Laboratory of Organometallic 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. 20272050). |
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| 摘 要： | Introduction Heteroatom-substituted 1,3-dienes have been exten-sively studied because of their marked abilities to con-struct highly functionalized ring systems in cycloaddi-tions.1 For example, Danishefsky2 developed 1-methoxy-3-trimethyl-siloxy-buta-1,3-diene which has led to many creative applications in complex organic synthesis. Padwa et al.3 demonstrated that 1,3- and 2, 3-bis(phenyl-sulfonyl)-1,3-butadienes are versatile building blocks in organic synthesis via reactions such as 4+2]-c…
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| 关 键 词： | 烯丙基乙醇 苯硒 p-甲苯基磺酰 1，3-二烯烃 立体选择性 |
Highly Stereoselective Synthesis of Phenylseleno-and p-Tolylsulfonyl Substituted 1,3-Dienes from Functionalized Allyl Alcohols |
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| XIE,Mei-Huaa,b HUANG,Xian,a,c a.Highly Stereoselective Synthesis of Phenylseleno- and p-Tolylsulfonyl Substituted 1,3-Dienes from Functionalized Allyl Alcohols[J].Chinese Journal of Chemistry,2004,22(2):184-186. |
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| Authors: | XIE Mei-Huaa b HUANG Xian a c a |
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| Institution: | Xixi Campus |
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| Abstract: | Phenylseleno‐ and p‐tolylsulfonyl substituted 1,3‐dienes were conveniently prepared with high stereoselectivity by the elimination reaction of phenylseleno‐ and p‐tolylsulfonyl substituted allyl alcohols in the presence of BF3 · Et2O in acetic anhydride. The products were characterized by 1H NMR, MS, IR and elemental analysis. The single crystal structure of 2a was determined by X‐ray diffraction analysis. |
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| Keywords: | allyl alcohol phenylseleno p-tolylsulfonyl 1 3-diene stereoselectivity |
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