| Evans手性助剂控制的不对称Michael加成立体选择性研究(Ⅱ) |
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| 引用本文： | 樊会丹,张从海,严胜骄,林军.Evans手性助剂控制的不对称Michael加成立体选择性研究(Ⅱ)[J].有机化学,2012,32(1):160-164. |
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| 作者姓名： | 樊会丹 张从海 严胜骄 林军 |
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| 作者单位： | 云南大学化学科学与工程学院 教育部自然资源药物化学重点实验室 昆明650091 |
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| 基金项目： | 国家自然科学基金，云南省自然科学基金 |
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| 摘 要： | 手性助剂控制的不对称反应是不对称合成的重要方法之一.以Evans手性助剂控制的Michael受体1为底物,在FeCl3催化下,通过不同格式试剂对其进行Michael加成,一步反应得到了一系列含两个手性中心的Michael加成产物2a～2h.获得了较高的立体选择性,其中化合物2d和2e得到了de值高达98%的非对映选择性.研究结果表明,亲核试剂的空间位阻是影响产物立体选择性的主要因素.
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| 关 键 词： | 不对称Michael加成 Evans手性助剂 非对映选择性 |
Asymmetric Michael Addition Reaction under the Control of the Evans Chiral Auxiliary (Ⅱ) |
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| Fan,Huidan
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Zhang,Conghai
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Yan,Shengjiao
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Lin,Jun.Asymmetric Michael Addition Reaction under the Control of the Evans Chiral Auxiliary (Ⅱ)[J].Chinese Journal of Organic Chemistry,2012,32(1):160-164. |
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| Authors: | Fan Huidan Zhang Conghai Yan Shengjiao Lin Jun |
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| Institution: | Fan,Huidan Zhang,Conghai Yan,Shengjiao Lin,Jun(Key Laboratory of Medicinal Chemistry for Natural Resources,Ministry of Education,School of Chemical Science and Technology,Yunnan University,Kunming 650091) |
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| Abstract: | Chiral auxiliaries controlled asymmetric reaction is one of the main methods in asymmetric synthesis.Under the control of the Evans auxiliary and catalyzed by FeCl3,different Grignard reagents were added asymmetrically to the substrates 1 by the way of 1,4-Michael addition reaction,and a series of Michael addition products 2a～2h which containing two chiral centers have been synthesized with higher stereoselectivity.Among them,compounds 2d and 2e achieved high diastereospeci-fically up to 98% de.The results showed that the steric hindrance of the Grignard reagents is the main factor which influences the stereoselectivity of Micheal addition. |
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| Keywords: | asymmetric Michael addition Evans chiral auxiliary diastereoselectivity |
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