Development of hybrid domino reactions via multi-chemical species and the synthetic application

多化学物质混合多米诺反应的发展及其合成应用

• 批准号: 20390008
• 负责人: NAITO Takeaki
• 金额: $ 12.31万
• 依托单位: Kobe Pharmaceutical University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (B)
• 财政年份: 2008
• 资助国家: 日本
• 起止时间: 2008 至 2010
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-20390008/
• 关键词: ラジカル種; イオン種; ドミノ反応; オキシムエーテル; 環境重視型反応; ラジカル; イオン; テオン; カキシムエーテル

Hybrid-type domino radical reactions of conjugated imine as a conjugated p-system were newly developed via the route involving various types of chemical species such as radical, ion, and organometallic species. Efficient synthetic methodology for highly functionalized products was developed via environmentally benign oxidation and radical-ionic domino reaction both of which proceeded via trapping the intermediates by atmospheric oxygen and appropriate electrophiles. Particularly, we were able to isolate unexpected reaction intermediates and thus succeeded in the development of powerful synthetic methods for various types of versatile and potential compounds by only one-manipulation.

共轭亚胺作为共轭p-体系的杂化型多米诺自由基反应是近年来发展起来的一种涉及自由基、离子和有机金属物种等多种化学物种的新途径。通过环境友好的氧化反应和自由基-离子多米诺反应，这两种反应都是通过大气氧气和适当的亲电试剂捕获中间体来进行的，从而开发了高效的高功能化产物的合成方法。特别是，我们能够分离出意想不到的反应中间体，从而成功地开发了强大的合成方法，用于各种类型的通用和潜在的化合物，只需一次操作。

项目成果

Efficient entry into 2-substituted tetrahydroquinoline systems through alkylative ring expansion: stereoselective formal synthesis of (+/-)-martinellic acid.

• DOI: 10.1021/jo902540x
• 发表时间: 2010-01
• 期刊: The Journal of organic chemistry
• 作者: Masafumi Ueda;S. Kawai;Masataka Hayashi;T. Naito*;O. Miyata

Regioselective Hydroxysulfenylation of α, β-Unsaturated Imines : Enhanced Stability of an Intermediate Radical.

α, β-不饱和亚胺的区域选择性羟基磺酰化：增强中间自由基的稳定性。

• 发表时间: 2008
• 期刊: Angew. Chem., Int. Ed. 47
• 作者: M. Ueda;H. Miyabe;H. Shimizu;H. Sugino;O. Miyata;T. Naito.
• 通讯作者: T. Naito.

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Aerobic Hydroxylation of N-Borylenamine: Triethylborane-mediated Hydroxyalkylation of α, β-Unsaturated Oxime Ether.

N-Borylenamine 的有氧羟基化：三乙基硼烷介导的 α, β-不饱和肟醚的羟烷基化。

• 发表时间: 2009
• 期刊: Org. Lett. 11
• 作者: Ueda;M.; Miyabe;H.; Kimura;T.; Kondoh;E.; Naito;T.; Miyata;O.
• 通讯作者: O.

DIRECT SYNTHESIS OF ISOXAZOLES VIA DOMINO REACTION OF ALKYNYL OXIMEETHERS

炔基肟醚多米诺反应直接合成异恶唑

• 发表时间: 2010
• 作者: Masaru Mori;Kohei Abe;Hiroaki Yamaguchi;Junichi Goto;Miki Shimada;Nariyasu Mano;内藤猛章
• 通讯作者: 内藤猛章