Formal Asymmetric Organocatalytic [3+2] Cyclization between Enecarbamates and 3-Indolylmethanols: Rapid Access to 3-Aminocyclopenta[b]indoles

Lebee Clement; Kataja Antti O.; Blanchard Florent; Masson Geraldine

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Formal Asymmetric Organocatalytic [3+2] Cyclization between Enecarbamates and 3-Indolylmethanols: Rapid Access to 3-Aminocyclopenta[b]indoles

机译：烯草胺和3-吲哚甲醇之间的形式不对称有机催化[3 + 2]环化：快速获得3-氨基环戊[b]吲哚

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摘要

A highly enantio- and diastereoselective synthesis of 3-aminocyclopenta[b]indoles has been developed through formal [3+2] cycloaddition reaction of enecarbamates and 3-indolylmethanols. This transformation is catalyzed by a chiral phosphoric acid that achieves simultaneous activation of both partners of the cycloaddition. Mechanistic data are also presented that suggest that the reaction occurs through a stepwise pathway.

机译：通过氨基甲酸酯和3-吲哚基甲醇的正式[3 + 2]环加成反应，已经开发了3-氨基环戊[b]吲哚的高度对映体和非对映体选择性。该转化由手性磷酸催化，该手性磷酸实现了环加成的两个伙伴的同时活化。还提供了机理数据，表明该反应通过逐步途径发生。

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《Chemistry: A European journal》 |2015年第23期|共4页
作者
Lebee Clement; Kataja Antti O.; Blanchard Florent; Masson Geraldine;
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正文语种 eng
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asymmetric synthesis; chirality; cycloaddition; enamide; iminium; indoles;

机译：不对称合成手性环加成酰胺亚胺吲哚;

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1. Formal Asymmetric Organocatalytic [3+2] Cyclization between Enecarbamates and 3-Indolylmethanols: Rapid Access to 3-Aminocyclopenta[b]indoles [J] . Lebee Clement, Kataja Antti O., Blanchard Florent, Chemistry: A European journal . 2015,第23期

机译：烯草胺和3-吲哚甲醇之间的形式不对称有机催化[3 + 2]环化：快速获得3-氨基环戊[b]吲哚
2. Organocatalytic Asymmetric Cyclization Reaction of 2-Alkynyl-3,3-Difluoro-3H-Indoles and 2-Mercaptoimidazoles: Access to gem-Difluorinated C2-Spiro Indolines [J] . Luo Jian, Fang Yu-Bo, Mao Xiang-Yu, Advanced synthesis & catalysis . 2019,第6期

机译：2-炔基-3,3-二氟-3H-吲哚和2-巯基咪唑的有机催化不对称环化反应：进入宝石 - 二氟化C2-螺吲哚吲哚
3. Palladium-Catalyzed Dynamic Kinetic Asymmetric Transformations of Vinyl Aziridines with Nitrogen Heterocycles: Rapid Access to Biologically Active Pyrroles and Indoles [J] . Barry M. Trost, Maksim Osipov, Guangbin Dong Journal of the American Chemical Society . 2010,第44期

机译：氮杂环催化钯催化乙烯基氮丙啶的动态动力学不对称转化：快速获得生物活性吡咯和吲哚类化合物
4. Part I. Asymmetric organocatalysis: (1) Direct enantioselective organocatalytic hydroxymethylation of aldehydes catalyzed by alpha,alpha-diphenylprolinol trimethylsilyl ether: Application in the formal synthesis of (-)-Rasfonin; (2) Synthesis of a novel bicyclic secondary amine organocatalyst: Application to the direct enantioselective organocatalytic hydroxymethylation of aldehydes. Part II. Asymmetric synthesis of bicyclic analogues of the anti-osteoporotic drug risedronate. [D] . Miller, John Robert. 2010

机译：第一部分，不对称有机催化：（1）α，α-二苯基脯氨醇三甲基甲硅烷基醚催化的醛的直接对映选择性有机催化羟甲基化：在（-）-Rasfonin的正式合成中的应用；（2）新型双环仲胺有机催化剂的合成：应用于醛的直接对映选择性有机催化羟甲基化。第二部分抗骨质疏松药物Risedronate的双环类似物的不对称合成。
5. Palladium-Catalyzed Dynamic Kinetic Asymmetric Transformations of Vinyl Aziridines with Nitrogen Heterocycles: Rapid Access to Biologically Active Pyrroles and Indoles [O] . Barry M. Trost, Maksim Osipov, Guangbin Dong -1

机译：与氮杂环乙烯彭孝军钯催化动态动力学不对称转化：快速访问具有生物活性的吡咯和吲哚
6. Asymmetric Organocatalytic Friedel-Crafts Alkylation-Cyclization Cascade Reaction of Indoles with o-Hydroxyaromatic α,β-Unsaturated Aldehydes [O] . Sung-Hyuk Gwon, Shin-Ae Kim, Sung-Gon Kim 2011

机译：非对称有机催化剂Friedel-Crafts烷基化环化吲哚与O-羟基芳族α，β-不饱和醛的反应

Formal Asymmetric Organocatalytic [3+2] Cyclization between Enecarbamates and 3-Indolylmethanols: Rapid Access to 3-Aminocyclopenta[b]indoles

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