Asymmetric tandem hemiaminal-heterocyclization-aza-Mannich reaction of 2-formylbenzonitriles and amines using chiral phase transfer catalysis: an experimental and theoretical study

Capobianco Amedeo; Di Mola Antonia; Intintoli Valentina; Massa Antonio; Capaccio Vito; Roiser Lukas; Waser Mario; Palombi Laura

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Asymmetric tandem hemiaminal-heterocyclization-aza-Mannich reaction of 2-formylbenzonitriles and amines using chiral phase transfer catalysis: an experimental and theoretical study

机译：使用手性相转移催化的非对称串联半硅杂环 - 2-甲酰苯并硝基苯和胺的反应：一种实验与理论研究

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The first asymmetric synthesis of 3-amino-substituted isoindolinones was accomplished via cascade hemiaminal-heterocyclization-intramolecular aza-Mannich reaction of benzylamines and 2-formylbenzonitriles using chiral phase transfer conditions (PTC). A theoretical study of the enantioselective step provides a rationale for the mode of action of the best performing phase transfer catalyst and the observed face selectivity.

机译：使用手性相转移条件（PTC）通过甲苄胺和2--甲酰甲腈的分子分子AZA-MANNICH-分子分子反应完成的第一个不对称合成。使用手性相转移条件（PTC）来完成3-氨基取代的异吲哚啉酮。对映选择性步骤的理论研究为最佳性能的相转移催化剂和观察到的面部选择性的作用方式提供了基本原理。

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来源
《RSC Advances》 |2016年第38期|共10页
作者
Capobianco Amedeo; Di Mola Antonia; Intintoli Valentina; Massa Antonio; Capaccio Vito; Roiser Lukas; Waser Mario; Palombi Laura;
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作者单位

Univ Salerno Dipartimento Chim &

Biol Via Giovanni Paolo II I-84084 Fisciano SA Italy;

Univ Salerno Dipartimento Chim &

Biol Via Giovanni Paolo II I-84084 Fisciano SA Italy;

Univ Salerno Dipartimento Chim &

Biol Via Giovanni Paolo II I-84084 Fisciano SA Italy;

Univ Salerno Dipartimento Chim &

Biol Via Giovanni Paolo II I-84084 Fisciano SA Italy;

Univ Salerno Dipartimento Chim &

Biol Via Giovanni Paolo II I-84084 Fisciano SA Italy;

Johannes Kepler Univ Linz Inst Organ Chem Altenberger Str 69 A-4040 Linz Austria;

Johannes Kepler Univ Linz Inst Organ Chem Altenberger Str 69 A-4040 Linz Austria;

Univ Salerno Dipartimento Chim &

Biol Via Giovanni Paolo II I-84084 Fisciano SA Italy;

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正文语种 eng
中图分类化学;
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1. Asymmetric tandem hemiaminal-heterocyclization-aza-Mannich reaction of 2-formylbenzonitriles and amines using chiral phase transfer catalysis: an experimental and theoretical study [J] . Capobianco Amedeo, Di Mola Antonia, Intintoli Valentina, RSC Advances . 2016,第38期

机译：使用手性相转移催化的非对称串联半硅杂环 - 2-甲酰苯并硝基苯和胺的反应：一种实验与理论研究
2. Asymmetric Aza-Henry Reaction Under Phase Transfer Catalysis: An Experimental and Theoretical Study [J] . Enrique Gomez-Bengoa, Anthony Linden, Rosa Lopez, Journal of the American Chemical Society . 2008,第25期

机译：相转移催化下的不对称氮杂-亨利反应的实验和理论研究
3. CATALYTIC ASYMMETRIC MICHAEL REACTION UNDER PHASE-TRANSFER CATALYSIS;CONSTRUCTION OF CHIRAL TETRASUBSTITUTED CARBON AND ITS APPLICATION TO THE SYNTHESIS OF A CHIRAL PYRROLIDONE [J] . Shigeru Arai, Fumie Takahashi, Riichiro Tsuji, Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry . 2006,第2期

机译：相转移催化下的催化不对称迈克尔反应;手性四取代碳的合成及其在手性吡咯烷酮合成中的应用
4. A Crystal Structure of the R-Amine Transaminase from Arthrobacter for Asymmetric Catalysis of Chiral Amines [C] . Lijun Guan, Nina Ji, Qinghong Meng, . 2018

机译：节杆菌的R-胺转氨酶的晶体结构用于手性胺的不对称催化
5. STUDIES IN ORGANOSULFUR CHEMISTRY. I. NUCLEAR MAGNETIC RESONANCE (PROTON, CARBON-13, OXYGEN-17 (1) J(C-H)) INVESTIGATIONS OF ORGANOSULFUR COMPOUNDS. II. MECHANISTIC STUDY OF PHASE TRANSFER CATALYZED REACTIONS OF DICHLOROCARBENE WITH SULFIDES AND SULFOXIDES. III. STUDIES DIRECTED TOWARD ASYMMETRIC SYNTHESIS USING CHIRAL PHASE TRANSFER CATALYSTS. [D] . DYER, JOHN COLLINS. 1980

机译：有机硫化学研究。 I.有机硫化合物的核磁共振（质子，碳13，氧17（1）J（C-H））研究。二。二氯卡宾与硫化物和硫化物的相转移催化反应的机理研究。三，使用手性相转移催化剂进行不对称合成的研究。
6. Asymmetric Catalysis Special Feature Part I: Enantioselective syntheses and biological studies of aeruginosin 298-A and its analogs: Application of catalytic asymmetric phase-transfer reaction [O] . Yuhei Fukuta, Takashi Ohshima, Vijay Gnanadesikan, 2004

机译：不对称催化特征第一部分：铜绿菌素298-A及其类似物的对映选择性合成和生物学研究：催化不对称相转移反应的应用
7. Asymmetric tandem hemiaminal-heterocyclization-aza-Mannich reaction of 2-formylbenzonitriles and amines using chiral phase transfer catalysis: an experimental and theoretical study [O] . Capobianco, Amedeo, Di Mola, Antonia, Intintoli, Valentina, 2016

机译：使用手性相转移催化的2-甲酰基苯甲腈和胺的不对称串联半缩醛胺 - 杂环化 - 氮杂 - 曼尼希反应：实验和理论研究

Asymmetric tandem hemiaminal-heterocyclization-aza-Mannich reaction of 2-formylbenzonitriles and amines using chiral phase transfer catalysis: an experimental and theoretical study

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