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Dynamic Resolution of Boronic Esters: A Powerful Strategy for Asymmetric Atropisomer Synthesis

硼酯的动态拆分：不对称阻转异构体合成的强大策略

基本信息

批准号：
EP/S018336/1
负责人：
Joseph Harrity
金额：
$ 48.15万
依托单位：
University of Sheffield
依托单位国家：
英国
项目类别：
Research Grant
财政年份：
2019
资助国家：
英国
起止时间：
2019 至无数据
项目状态：
已结题

来源：
https://gtr.ukri.org/projects?ref=EP%2FS018336%2F1
关键词：
Dynamic Resolution Boronic Esters Powerful

项目摘要

Atropisomers are an unusual class of molecules in organic chemistry as they convey a defined three-dimensional shape from flat molecular fragments. Atropisomerism arises from hindrance of bond rotation about single bonds due to steric clashes, thereby making the isolation of the individual isomers possible. There are a large number of prominent molecules derived from nature as well as pharmaceuticals that exhibit atropisomerism, however stereoselective synthetic methods towards these compounds remain very challenging. We have developed a way to access specific atropisomers with high selectivity that involves the equilibration of an easily prepared stereoisomeric mixture. This method is underpinned by the chemistry of boron, which serves to both control atropisomer stereochemistry, while acting as a handle for further chemical modifications. We are only just beginning to understand the scope of this process, but we believe that it will represent a general method for preparing these important compounds. The requested grant will allow us to demonstrate the potential of the methodology, and will show that we can use it to access a very broad range of high value chemicals.

阻转异构体在有机化学中是一类不寻常的分子，因为它们从扁平分子片段中传递出定义的三维形状。阻转异构现象是由于空间位阻阻碍了单键的键旋转，从而使分离单个异构体成为可能。存在大量源自自然界的突出分子以及表现出阻转异构性的药物，然而针对这些化合物的立体选择性合成方法仍然非常具有挑战性。我们开发了一种高选择性地获得特定阻转异构体的方法，该方法涉及平衡容易制备的立体异构体混合物。这种方法是由硼的化学，它既控制阻转异构体的立体化学，同时作为进一步的化学修饰的把手。我们只是刚刚开始了解这个过程的范围，但我们相信它将代表制备这些重要化合物的一般方法。申请的资助将使我们能够展示该方法的潜力，并表明我们可以使用它来获得非常广泛的高价值化学品。

项目成果

期刊论文数量（2）

专著数量（0）

科研奖励数量（0）

会议论文数量（0）

专利数量（0）

A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin

链黑素立体控制合成的动态热力学拆分策略

DOI：
10.1002/ange.202213692
发表时间：
2022
期刊：
Angewandte Chemie
影响因子：
0
作者：
Valdez Pérez L
通讯作者：
Valdez Pérez L

A Dynamic Thermodynamic Resolution Strategy for the Stereocontrolled Synthesis of Streptonigrin.

DOI：
10.1002/anie.202213692
发表时间：
2023-01-26
期刊：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
影响因子：
16.6
作者：
Perez, Luis F. Valdez;Bachollet, Sylvestre P. J. T.;Orlov, Nikolai V. V.;Kopf, Kenji P. M.;Harrity, Joseph P. A.
通讯作者：
Harrity, Joseph P. A.