- 标题
- 摘要
- 关键词
- 实验方案
- 产品
-
Towards the design of optically active thiophene S-oxides using quantum chemistry
摘要： The importance of axially chiral biaryls has risen steeply in the recent decades. This structural motif proved to be successful in catalytic asymmetric synthesis and the configuration of the biaryl axis is decisive for biological activity. A new approach for the atroposelective synthesis of biaryls would be through a cycloaddition between an enantiopure phenyl-substituted thiophene S-oxide and an alkyne. Importantly, the chiral center of the thiophene S-oxide needs to be stable enough to avoid pyramidal inversion during the cycloaddition. Since the racemization of thiophene monoxides has been scarcely investigated so far, we perform a thorough quantum chemical study on the inversion barriers of a large number of chiral thiophene S-oxide derivatives. Our main goal is to identify substitution patterns leading to stable atropisomers at room temperature. Appealingly, the role of the stereoelectronic effects and position of the substituents as well as the importance of aromaticity on the pyramidal inversion barrier is elucidated for the first time.
关键词： thiophene sulfoxides,axial chirality,DFT,enantiomerization,aromaticity
更新于2025-09-23 15:23:52
-
Chiral Carbazoles
摘要： Asymmetric Synthesis of Axially Chiral Benzocarbazole Derivatives Based on Catalytic Enantioselective Hydroarylation of Alkynes
关键词： cyclization,axial chirality,benzocarbazoles
更新于2025-09-23 15:21:21