Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N-Boc ketimines catalyzed by chiral phase-transfer catalysts

Liu Yuxin; Wang Jingdong; Wei Zhonglin; Cao Jungang; Liang Dapeng; Lin Yingjie; Duan Haifeng

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Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N-Boc ketimines catalyzed by chiral phase-transfer catalysts

机译：由手性相转移催化剂催化的Isatin衍生的N-BOC酮亚胺的非对映异构和对映选择性的硝基 - 甘地色反应

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A highly diastereo- and enantioselective nitro-Mannich reaction of isatin-derived ketimines with alpha-aryl nitromethane catalyzed by Cinchona alkaloid-derived phase-transfer catalysts bearing multiple hydrogen-bonding donors (the first metal-free catalytic systems used in this reaction) was developed. A series of 3-substituted 3-amino-oxindoles were constructed using this protocol in excellent yields (96-99%) with high enantioselectivities (up to 95% ee) and diastereo-selectivities (up to 95:5 dr).

机译：具有含有多个氢键供体的Cinchona生物碱衍生的相转移催化剂催化的α-芳基硝基甲烷的α-芳基硝基甲烷的高度自对氨基和对映选择性的硝基 - 曼尼希反应（在该反应中使用的第一个无金属催化系统）是发达。使用该方案使用该方案以优异的产量（96-99％）构建一系列3取代的3-氨基氧胆砂，具有高对映射性（高达95％）和非对映选择性（高达95：5 DR）。

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《New Journal of Chemistry》 |2018年第3期|共4页
作者
Liu Yuxin; Wang Jingdong; Wei Zhonglin; Cao Jungang; Liang Dapeng; Lin Yingjie; Duan Haifeng;
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Jilin Univ Coll Chem Dept Organ Chem 2699 Qianjin St Changchun 130012 Jilin Peoples R China;

Jilin Univ Coll Chem Dept Organ Chem 2699 Qianjin St Changchun 130012 Jilin Peoples R China;

Jilin Univ Coll Chem Dept Organ Chem 2699 Qianjin St Changchun 130012 Jilin Peoples R China;

Jilin Univ Coll Chem Dept Organ Chem 2699 Qianjin St Changchun 130012 Jilin Peoples R China;

Jilin Univ Coll Chem Dept Organ Chem 2699 Qianjin St Changchun 130012 Jilin Peoples R China;

Jilin Univ Coll Chem Dept Organ Chem 2699 Qianjin St Changchun 130012 Jilin Peoples R China;

Jilin Univ Coll Chem Dept Organ Chem 2699 Qianjin St Changchun 130012 Jilin Peoples R China;

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正文语种 eng
中图分类化学;
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1. Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N-Boc ketimines catalyzed by chiral phase-transfer catalysts [J] . Liu Yuxin, Wang Jingdong, Wei Zhonglin, New Journal of Chemistry . 2018,第3期

机译：由手性相转移催化剂催化的Isatin衍生的N-BOC酮亚胺的非对映异构和对映选择性的硝基 - 甘地色反应
2. Bis(imidazolidine)pyridine-NiCl_2 Catalyst for Nitro-Mannich Reaction of Isatin-Derived N-Boc Ketimines: Asymmetric Synthesis of Chiral 3-Substituted 3-Amino-2-oxindoles [J] . Takayoshi Arai, Eri Matsumura, Hyuma Masu Organic letters . 2014,第10期

机译：双（咪唑烷）吡啶-NiCl_2催化Isatin衍生的N-Boc酮亚胺的硝基-曼尼希反应：手性3-取代的3-氨基-2-氧吲哚的不对称合成
3. Bis(imidazolidine)pyridine-NiCl_2 Catalyst for Nitro-Mannich Reaction of Isatin-Derived N-Boc Ketimines: Asymmetric Synthesis of Chiral 3-Substituted 3-Amino-2-oxindoles [J] . Takayoshi Arai, Eri Matsumura, Hyuma Masu Organic letters . 2014,第10期

机译：双（咪唑烷）吡啶-NiCl_2催化Isatin衍生的N-Boc酮亚胺的硝基-曼尼希反应：手性3-取代的3-氨基-2-氧吲哚的不对称合成
4. Diastereo- and Enantioselective Henry Reaction Catalyzed by Sulfonyldiamine-CuCl-Pyridine System [C] . Yoko Endo, Ryuta Takashita, Akira Yanagisawa Symposium on Organometallic Chemistry . 2007

机译：硫胺二胺 - CuCl-吡啶体系催化的非对映异构和对映选择性的亨利反应
5. Synthesis of chiral catalysts: Structure enantioselectivity relationship studies of various (DHQD)2PHAL catalyzed halocyclizations and synthesis of novel C2-symmetric pyridine ligands. [D] . Marshall, Sarah Elizabeth. 2013

机译：手性催化剂的合成：各种（DHQD）2PHAL催化的卤代环化反应的结构对映选择性关系研究以及新型C2对称吡啶配体的合成。
6. N-Heterocyclic carbenes as chiral Brønsted base catalysts: a highly diastereo- and enantioselective 16-addition reaction [O] . Surojit Santra, Arka Porey, Barun Jana, 2018

机译：N-杂环卡宾作为手性布朗斯台德碱催化剂：高度非对映和对映选择性的16-加成反应
7. Rhodium-Catalyzed Enantioselective Addition of Arylboroxines to Isatin-Derived NBoc Ketimines Using Chiral PhosphiteOlefin Ligands: Asymmetric Synthesis of 3Aryl-3-amino-2-oxindoles [O] . -1

机译：使用手性磷酸酯配体，铑催化芳基硼溴芳基硼毒剂的氨基硼毒性加入甲基衍生的NBOC酮亚胺：3aryl-3-氨基-2-氧胆砂的不对称合成

Diastereo- and enantioselective nitro-Mannich reaction of isatin-derived N-Boc ketimines catalyzed by chiral phase-transfer catalysts

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