| Novel Method for the Enantioselective Synthesis of β-Lactams |
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| 作者姓名： | YUAN Qing JIAN Shan-zhong WANG Yan-guang |
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| 作者单位： | Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China |
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| 基金项目： | Supported by the National Natural Science Foundation of China（No. 20272051） and the Natural Science Foundation of Zhejiang Province, China（No. R404109）. |
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| 摘 要： | A novel method for the enantioselective synthesis of β-lactams is described in this study. 2,3-Dihydrobenzooxazin-4-one derived from salicylamide and L-menthone was used as the chiral auxiliary, which reacted with a-bromo-acyl bromides in the presence of pyridine to give carboximides 2. The stereo-controlled Reformatsky-type reactions of carboximides with imines yielded the corresponding trans β-lactams with high enantioselectivities（e.e. 75%-86%） and high chemical yields（63%-85%）, meanwhile, the chiral auxiliary dihydrobenzooxazin-4-one was released and recovered.
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| 关 键 词： | 化学结构 活性 药物 分析方法 内酰胺 |
| 收稿时间： | 2007-06-18 |
| 修稿时间： | 2007-09-13 |
Novel Method for the Enantioselective Synthesis of β-Lactams |
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| YUAN Qing JIAN Shan-zhong WANG Yan-guang.Novel Method for the Enantioselective Synthesis of β-Lactams[J].Chemical Research in Chinese University,2008,24(1):58-64. |
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| Authors: | Qing YUAN Shan-zhong JIAN Yan-guang WANG |
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| Institution: | aDepartment of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China |
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| Abstract: | A novel method for the enantioselective synthesis of β-lactams is described in this study. 2,3-Dihydrobenzooxazin-4-one derived from salicylamide and L-menthone was used as the chiral auxiliary, which reacted with  -bromo-acyl bromides in the presence of pyridine to give carboximides 2. The stereo-controlled Reformatsky-type reactions of carboximides with imines yielded the corresponding trans β-lactams with high enantioselectivities(e.e. 75%–86%) and high chemical yields(63%–85%), meanwhile, the chiral auxiliary dihydrobenzooxazin-4-one was released and recovered. |
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| Keywords: | β-Lactams Enantioselective Chiral auxiliary Reformatsky reaction |
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