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| 盐酸(R)-沙丁胺醇的不对称合成 | |
| 引用本文： | 程青芳,王启发,许兴友,叶燕斌,张辉.盐酸(R)-沙丁胺醇的不对称合成[J].有机化学,2007,27(12):1558-1561. |
| 作者姓名： | 程青芳 王启发 许兴友 叶燕斌 张辉 |
| 作者单位： | 1. 淮海工学院化工系,连云港,222005;南京理工大学材料化学实验室,南京,210094 2. 淮海工学院海洋学院,连云港,222005 3. 淮海工学院化工系,连云港,222005 |
| 基金项目： | 江苏省教育厅高校自然科学计划(No.05KJD150024)，淮海工学院自然科学研究基金(Nos.Z200521,22006011)资助项目. |
| 摘 要： | 研究了一种化学不对称合成盐酸(R)-沙丁胺醇的方法. 以自制的手性龙脑基β-二酮铁络合物为催化剂催化起始原料3-乙酰氧基甲基-4-乙酰氧基苯乙烯(1)的不对称环氧化, 得到(R)-3-乙酰氧基甲基-4-乙酰氧基苯基环氧乙烷(2), 这一步的化学收率和光学收率都较高. 然后环氧化合物2与叔丁胺发生开环反应, 再与盐酸成盐即制得盐酸(R)-沙丁胺醇. 合成盐酸(R)-沙丁胺醇只需两步, 总收率为68%. 还考察了反应温度、催化剂种类、催化剂的量等因素对3-乙酰氧基甲基-4-乙酰氧基苯乙烯(1)的不对称环氧化的化学产率和光学收率的影响. |
| 关 键 词： | 盐酸(R)-沙丁胺醇 龙脑基β-二酮 铁络合物 不对称环氧化 |
| 收稿时间： | 2007-03-06 |
| 修稿时间： | 2007-06-11 |
Enantioselective Synthesis of (R)-Salbutamol Hydrochloride |
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| CHENG,Qing-Fang,WANG,Qi-Fa,XU,Xing-You,YE,Yan-Bin,ZHANG,Hui.Enantioselective Synthesis of (R)-Salbutamol Hydrochloride[J].Chinese Journal of Organic Chemistry,2007,27(12):1558-1561. | |
| Authors: | CHENG Qing-Fang WANG Qi-Fa XU Xing-You YE Yan-Bin ZHANG Hui |
| Institution: | ( Department of Chemical Technology, Huaihai Institute of Technology, Lianyungang 222005)( Materials Chemistry Laboratory, Nanjing University of Science and Technology, Nanjing 210094)( College of Marine Science, Huaihai Institute of Technology, Lianyungang 222005) |
| Abstract: | The enantioselective synthesis of (R)-salbutamol hydrochloride was investigated. The asymmetric epoxidation of 3-acetoxymethyl-4-acetyloxystyrene (1) catalyzed by chiral camphyl β-diketone iron complex enantioselectively afforded (R)-3-acetoxymethyl-4-acetyloxy styrene oxide (2) in good yield and enantioselectivity. In following steps, styrene oxide 2 was converted into (R)-salbutamol hydrochloride in 68% overall yield via the ring-opening of chiral terminal styrene oxide 2 with t-butylamine and then with hydrochloride. Some factors effecting the yield and the enantioselectivity of asymmetric epoxidation of 3-acetoxymethyl-4- acetyloxystyrene (1) were discussed. |
| Keywords: | (R)-salbutamol hydrochloride camphyl β-diketone iron complex asymmetric epoxidation |
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