Efficient Direct Synthesis of Aziridine-Containing Chiral Tridentate Ligands by the Iminium-Mediated Self-Ring Opening Reaction of Enantiopure Aziridines and Salicylaldehydes

Chen Xingpeng; Lin Chao; Du Hongguang; Xu Jiaxi

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Efficient Direct Synthesis of Aziridine-Containing Chiral Tridentate Ligands by the Iminium-Mediated Self-Ring Opening Reaction of Enantiopure Aziridines and Salicylaldehydes

机译：高效地直接合成含有氨化亚齐齐齐齐齐齐和水杨醛的氨基型介导的自响开启反应的含氮葡聚胺的手性三齿配体

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摘要

An efficient method for the direct synthesis of aziridine-containing chiral tridentate ligands was developed from enantiopure aziridines and salicylaldehydes. The method achieved the regiospecific cleavage of more substituted C-N bonds of aziridines through an iminium-mediated self-ring opening reaction of aziridines with up to 95% yield and complete inversion of configuration. The (S)-2-alkylaziridine-derived tridentate ligands displayed excellent activity and stereoselectivity in the zinc trifluoromethanesulfonate-catalyzed asymmetric aldol reactions of acetone and aromatic aldehydes.

机译：一种有效的含氮氧基手性三齿配体的方法是从对映络氮化物和水杨醛产生的。该方法通过亚齐里丁的亚氨基介导的自环反应实现了偶氮红外的更取代的C-N键的再生性切割，其含有高达95％的产率和完全的构型。（S）-2-烷基氮杂氨酸衍生的三乙酸盐在三氟甲磺酸锌催化的丙酮和芳族醛的不对称醛醇反应中显示出优异的活性和立体选择性。

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来源
《Advanced synthesis & catalysis》 |2019年第7期|共15页
作者
Chen Xingpeng; Lin Chao; Du Hongguang; Xu Jiaxi;
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作者单位

Beijing Univ Chem Technol Fac Sci Dept Organ Chem State Key Lab Chem Resource Engn Beijing 100029 Peoples R China;

Beijing Univ Chem Technol Fac Sci Dept Organ Chem State Key Lab Chem Resource Engn Beijing 100029 Peoples R China;

Beijing Univ Chem Technol Fac Sci Dept Organ Chem State Key Lab Chem Resource Engn Beijing 100029 Peoples R China;

Beijing Univ Chem Technol Fac Sci Dept Organ Chem State Key Lab Chem Resource Engn Beijing 100029 Peoples R China;

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原文格式 PDF
正文语种 eng
中图分类化学工业;物理化学（理论化学）、化学物理学;化学反应过程;
关键词
iminium-mediated; self-ring opening; aziridine; chiral tridentate ligand; asymmetric aldol reaction;

机译：亚胺介导;自圈开口;Aziridine;手性三叉子配体;不对称醛醇反应;

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专利

1. Efficient Direct Synthesis of Aziridine-Containing Chiral Tridentate Ligands by the Iminium-Mediated Self-Ring Opening Reaction of Enantiopure Aziridines and Salicylaldehydes [J] . Chen Xingpeng, Lin Chao, Du Hongguang, Advanced synthesis & catalysis . 2019,第7期

机译：高效地直接合成含有氨化亚齐齐齐齐齐齐和水杨醛的氨基型介导的自响开启反应的含氮葡聚胺的手性三齿配体
2. Addition Reactions of Iodomethyllithium to Imines. A Direct and Efficient Synthesis of Aziridines and Enantiopure Amino Aziridines [J] . Concellon JM, Rodriguez-Solla H, Simal C Organic letters . 2008,第20期

机译：碘甲基锂与亚胺的加成反应。直接高效合成氮丙啶和对映体纯氨基氮丙啶
3. Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine [J] . Hogyu Lee, Jun Hee Kim, Won Koo Lee, Organic & biomolecular chemistry . 2013,第22期

机译：高度立体选择性的定向反应和从手性氮丙啶高效合成氮杂呋喃糖酶
4. Discovery of Chiral Tridentate Titanium Catalysts for Enantioselective HAD Reaction through Ligand and Additive Diversity:Dramatic Effect of Carboxylic Acids [C] . Yu Yuan Proceedings of the First China-Korea symposium on organic chemistry . 2001

机译：通过配体和添加剂多样性对手性三齿钛催化剂进行对映选择性HAD反应的发现：羧酸的剧烈作用
5. Efficient discovery of chiral catalysts for asymmetric reactions by modular ligand design, solid-phase synthesis, and high-throughput determination of enantiomeric excess. [D] . Sprout, Christopher M. 2006

机译：通过模块化配体设计，固相合成和对映体过量的高通量测定，有效发现了用于不对称反应的手性催化剂。
6. Asymmetric Intermolecular Boron Heck-Type Reactions via Oxidative Palladium(II) Catalysis Using Chiral Tridentate NHC-Amidate-Alkoxide Ligands [O] . Kyung Soo Yoo, Justin O’Neill, Satoshi Sakaguchi, -1

机译：通过氧化钯（II）使用手性三乙酸NHC-氨基酯 - 醇盐配体通过氧化钯（II）催化的不对称分子间硼型反应
7. Synthesis of chiral 1-(2-aminoalkyl)aziridines via the self-opening reaction of aziridine [O] . Adam M. Pieczonka, Ewelina Misztal, Michał Rachwalski, 2016

机译：通过氮丙啶的自开合反应合成手性1-（2-氨基烷基）氮丙啶

Efficient Direct Synthesis of Aziridine-Containing Chiral Tridentate Ligands by the Iminium-Mediated Self-Ring Opening Reaction of Enantiopure Aziridines and Salicylaldehydes

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