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手性联苯型化合物的对映选择性合成。

Enantioselective synthesis of chiral BCPs.

作者信息

Sánchez-Sordo Irene, Barbeira-Arán Sergio, Fañanás-Mastral Martín

机构信息

Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Universidade de Santiago de Compostela 15782 Santiago de Compostela Spain

出版信息

Org Chem Front. 2023 Dec 21;11(3):916-928. doi: 10.1039/d3qo01631e. eCollection 2024 Jan 30.

DOI:10.1039/d3qo01631e
PMID:38298565
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10825854/
Abstract

Bicyclo[1.1.1]pentanes (BCPs) have emerged as an interesting scaffold in drug design. These strained molecules can act as bioisosteres of -substituted phenyl rings, -butyl groups or internal alkynes, leading to drug analogues with enhanced pharmacokinetic and physicochemical properties. Thus, catalytic methodologies for the synthesis of BCPs represent a major goal in modern organic synthesis. In particular, asymmetric transformations that provide chiral BCPs bearing an adjacent stereocenter are particularly valuable to expand the chemical space of this important scaffold. In this article, we discuss the available methodologies for the asymmetric synthesis of α-chiral BCPs, their key mechanistic features and their application in bioisosteric replacements in drug design.

摘要

双环[1.1.1]戊烷（BCPs）已成为药物设计中一种有趣的骨架。这些张力分子可作为α-取代苯环、叔丁基或内炔的生物电子等排体，从而得到具有增强药代动力学和物理化学性质的药物类似物。因此，BCPs的催化合成方法是现代有机合成的一个主要目标。特别是，提供带有相邻立体中心的手性BCPs的不对称转化对于扩展这个重要骨架的化学空间尤为重要。在本文中，我们讨论了α-手性BCPs不对称合成的可用方法、其关键的机理特征以及它们在药物设计中生物电子等排体替代方面的应用。

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