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轴向轴向非对映体还原催化合成含1,2重氮的邻三苯阿托品
作者:小柯机器人 发布时间:2021/5/15 15:37:30

武汉大学周强辉团队报道了轴向轴向非对映体还原催化合成含1,2重氮的邻三苯阿托品。 相关论文于2021年5月7日发表于国际顶尖学术期刊《美国化学会杂志》杂志上。

该文中,研究人员报道了一种通过钯/手性降冰片烯协同催化和轴向-轴向非对映体还原将阿托品异构体邻三苯基与1,2-重离子组装的模块化和聚合策略。容易获得的芳基碘化物、2,6-取代的芳基溴化物和芳基三氟硼酸钾用作砌块,为这些支架的多样性取向合成奠定了基础(46个例子)。其他特点包括独特的轴向到轴向非对映体模式,在一次操作中建造两个轴,以及步进经济性。通过DFT计算以使轴向到轴向非对映体还原过程合理化。

研究工作证明了该方法在制备阿托品寡苯、手性催化剂和配体方面的实用性。

附:英文原文

Title: Catalytic Synthesis of Atropisomeric o-Terphenyls with 1,2-Diaxes via Axial-to-Axial Diastereoinduction

Author: Qianwen Gao, Chenggui Wu, Shuang Deng, Lisha Li, Ze-Shui Liu, Yu Hua, Jinxiang Ye, Chang Liu, Hong-Gang Cheng, Hengjiang Cong, Yinchun Jiao, Qianghui Zhou

Issue&Volume: May 7, 2021

Abstract: Herein, we report a modular and convergent strategy for the assembly of atropisomeric o-terphenyls with 1,2-diaxes via palladium/chiral norbornene cooperative catalysis and axial-to-axial diastereoinduction. Readily available aryl iodides, 2,6-substituted aryl bromides, and potassium aryl trifluoroborates are used as the building blocks, laying the foundation for diversity-oriented synthesis of these scaffolds (46 examples). Other features include the unique axial-to-axial diastereoinduction mode, construction of two axes in a single operation, and step economy. DFT calculations are performed to rationalize the axial-to-axial diastereoinduction process. Synthetic utilities of this method in preparation of atropisomeric oligophenyls, chiral catalysts, and ligands are demonstrated.

DOI: 10.1021/jacs.1c02405

Source: https://pubs.acs.org/doi/10.1021/jacs.1c02405

 

期刊信息

JACS:《美国化学会志》,创刊于1879年。隶属于美国化学会,最新IF:14.612
官方网址:https://pubs.acs.org/journal/jacsat
投稿链接:https://acsparagonplus.acs.org/psweb/loginForm?code=1000