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轴向立体富集联芳基的合成新进展和新概念。

Recent advances and new concepts for the synthesis of axially stereoenriched biaryls.

机构信息

Laboratoire de Chimie Moléculaire, UMR CNRS 7509, SynCat, Université de Strasbourg, ECPM, 25 rue Becquerel, 67087, Strasbourg, France.

出版信息

Chem Soc Rev. 2015 Jun 7;44(11):3418-30. doi: 10.1039/c5cs00012b.

Abstract

Axial chirality is a key feature of many important organic molecules, such as biologically active compounds, stereogenic ligands and optically pure materials. Significant efforts in the field of the atropisomeric synthesis of biaryls have hence been undertaken over the past decade. Several major improvements of the already known methods to build up such chiral backbones (e.g. oxidative couplings and stereoselective Suzuki-Miyaura arylations) have been achieved and, in parallel, novel concepts have emerged enabling unprecedented synthetic routes toward molecules of this kind. These outstanding steps further unlocked the door to the preparation of previously difficult-to-access precursors of privileged ligands like BINOL, BINAM, QUINAP and many other molecules of interest.

摘要

轴手性是许多重要有机分子的关键特征,例如生物活性化合物、手性配体和光学纯材料。因此,在过去的十年中,人们在联芳基的对映选择性合成领域做出了重大努力。已经实现了对构建此类手性骨架的已有方法(例如氧化偶联和立体选择性 Suzuki-Miyaura 芳基化)的几项重大改进,并且同时出现了新的概念,从而为这种类型的分子开辟了前所未有的合成途径。这些杰出的步骤进一步为制备以前难以获得的优势配体(如 BINOL、BINAM、QUINAP 和许多其他有兴趣的分子)的前体打开了大门。

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