Computational Evidence for the Enamine Mechanism of Intramolecular Aldol Reactions Catalyzed by Proline

Fernando R.Clemente; K.N.Houk

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Computational Evidence for the Enamine Mechanism of Intramolecular Aldol Reactions Catalyzed by Proline

机译：脯氨酸催化的分子内羟醛反应烯胺机理的计算证据

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The first examples of enantioselective intramolecular aldol cyclizations catalyzed by proline (Scheme 1) were independently reported by Hajos and Parrish and by Wiechert and co-workers in 1971.Useful synthetic intermediates,such as the Wieland-Miescher ketone (3 b) are easily obtained by this reaction.This reaction constitutes a cornerstone in the emergent field of enantioselective organocatalysis.

机译：脯氨酸催化的对映选择性分子内羟醛缩环反应的第一个例子（方案1）由Hajos和Parrish以及Wiechert和他的同事于1971年独立报告，很容易获得有用的合成中间体，例如Wieland-Miescher酮（3b）。该反应构成了对映选择性有机催化新兴领域的基石。

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《Angewandte Chemie》 |2004年第43期|共3页
作者
Fernando R.Clemente; K.N.Houk;
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正文语种 eng
中图分类应用化学;
关键词
aldol reaction; asymmetric catalysis; density functional calculations; proline; reaction mechanisms;

机译：羟醛反应;不对称催化;密度泛函计算;脯氨酸;反应机理;

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1. Computational Evidence for the Enamine Mechanism of Intramolecular Aldol Reactions Catalyzed by Proline [J] . Fernando R.Clemente, K.N.Houk Angewandte Chemie . 2004,第43期

机译：脯氨酸催化的分子内羟醛反应烯胺机理的计算证据
2. Enamine versus Oxazolidinone: What Controls Stereoselectivity in Proline-Catalyzed Asymmetric Aldol Reactions?† [J] . li id=au1Akhilesh#x2005, K. Sharma li id=au2Raghavan#x2005, B. Sunoj Prof.#x2005, Angewandte Chemie . 2010,第36期

机译：烯胺与恶唑烷酮：脯氨酸催化的不对称醛醇缩合反应中控制立体选择性的因素是什么？†
3. Enamine versus Oxazolidinone: What Controls Stereoselectivity in Proline-Catalyzed Asymmetric Aldol Reactions?† [J] . Akhilesh#x2005, K. Sharma Raghavan#x2005, B. Sunoj Prof.#x2005, Angewandte Chemie International Edition . 2010,第36期

机译：烯胺与恶唑烷酮：脯氨酸催化的不对称醛醇缩合反应中控制立体选择性的因素是什么？†
4. Theoretical investigation on the role of amine bases in stabilizing the key intermediate of proline enamine carboxylate in proline-catalyzed asymmetric reactions [C] . Changke Tian, Aiping Fu, Chengyan Zhao International Conference on Applied Sciences, Engineering and Technology . 2014

机译：胺基碱在脯氨酸催化不对称反应中脯氨酸烯胺羧酸盐关键中间体作用的理论研究
5. Part I: Total Synthesis of Marine Macrolide Amphidinolide F and Synthetic Studies Toward Amphidinolide C; Part II: Computational Study on Proline Sulfonamide-catalyzed Aldol Reaction. [D] . Mahapatra, Subham. 2013

机译：第一部分：海洋大环内酯Amphidinolide F的全合成及对Amphidinolide C的合成研究；第二部分：脯氨酸磺酰胺催化的羟醛反应的计算研究。
6. Rate Limiting Step Precedes C–C Bond Formation in the Archetypical Proline-Catalyzed Intramolecular Aldol Reaction [O] . Hui Zhu, Fernando R. Clemente, K. N. Houk, -1

机译：速率限制步骤先于典型脯氨酸催化的分子内羟醛反应中的CC键形成
7. Brønsted Acids as Additives for the Direct Asymmetric Aldol Reaction Catalyzed byl-Prolinethioamides. Direct Evidence for Enamine−Iminium Catalysis. [O] . Dorota Gryko, Magdalena Zimnicka, Radosław Lipiński 2007

机译：Brønsted酸作为直接非对称醛醇反应的添加剂催化ByL-脯氨酸反应。烯胺 - 亚胺催化的直接证据。

Computational Evidence for the Enamine Mechanism of Intramolecular Aldol Reactions Catalyzed by Proline

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