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Enantioselective Synthesis of Heteroatom‐Linked Non‐Biaryl Atropisomers
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2024-05-15 , DOI: 10.1002/anie.202407767
Abdelati Naghim 1 , Jean RODRIGUEZ 2 , Olivier Chuzel 1 , Gaëlle Chouraqui 1 , Damien Bonne 3
Affiliation  

Atropisomers hold significant fascination, not only for their prevalence in natural compounds but also for their biological importance and wide‐ranging applications as chiral materials, ligands, and organocatalysts. While biaryl and heterobiaryl atropisomers are commonly studied, the enantioselective synthesis of less abundant heteroatom‐linked non‐biaryl atropisomers presents a formidable challenge in modern organic synthesis. Unlike classical atropisomers, these molecules allow rotation around two bonds, resulting in low barriers to enantiomerization through concerted bond rotations. In recent years the discovery of new configurationally stable rare non‐biaryl scaffolds such as aryl amines, aryl ethers and aryl sulfones as well as innovative methodologies to control their configuration have been disclosed in the literature and constitute the topic of this minireview.

中文翻译:


杂原子连接的非联芳基阻转异构体的对映选择性合成



阻转异构体具有巨大的吸引力,不仅因为它们在天然化合物中普遍存在,还因为它们的生物学重要性以及作为手性材料、配体和有机催化剂的广泛应用。虽然联芳基和杂联芳基阻转异构体被广泛研究,但对映选择性合成不太丰富的杂原子连接的非联芳基阻转异构体在现代有机合成中提出了巨大的挑战。与经典的阻转异构体不同,这些分子允许围绕两个键旋转,从而通过协调的键旋转降低对映异构化的障碍。近年来,文献中公开了新的构型稳定的稀有非联芳基支架(例如芳基胺、芳基醚和芳基砜)的发现以及控制其构型的创新方法,并构成了本次小型综述的主题。
更新日期:2024-05-15
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