C(sp)-C(sp) Lever-Based Targets of Orientational Chirality: Design and Asymmetric Synthesis

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dc.creatorXu, Ting
dc.creatorWang, Jia Yin
dc.creatorWang, Yu
dc.creatorJin, Shengzhou
dc.creatorTang, Yao (TTU)
dc.creatorZhang, Sai (TTU)
dc.creatorYuan, Qingkai (TTU)
dc.creatorLiu, Hao (TTU)
dc.creatorYan, Wenxin
dc.creatorJiao, Yinchun
dc.creatorYang, Xiao Liang
dc.creatorLi, Guigen (TTU)
dc.date.accessioned2024-06-18T20:11:34Z
dc.date.available2024-06-18T20:11:34Z
dc.date.issued2024
dc.description© 2024 by the authors. cc-by
dc.description.abstractIn this study, the design and asymmetric synthesis of a series of chiral targets of orientational chirality were conducted by taking advantage of N-sulfinylimine-assisted nucleophilic addition and modified Sonogashira catalytic coupling systems. Orientational isomers were controlled completely using alkynyl/alkynyl levers [C(sp)-C(sp) axis] with absolute configuration assignment determined by X-ray structural analysis. The key structural element of the resulting orientational chirality is uniquely characterized by remote through-space blocking. Forty examples of multi-step synthesis were performed, with modest to good yields and excellent orientational selectivity. Several chiral orientational amino targets are attached with scaffolds of natural and medicinal products, showing potential pharmaceutical and medical applications in the future.
dc.identifier.citationXu, T., Wang, J.-Y., Wang, Y., Jin, S., Tang, Y., Zhang, S., Yuan, Q., Liu, H., Yan, W., Jiao, Y., Yang, X.-L., & Li, G.. 2024. C(sp)-C(sp) Lever-Based Targets of Orientational Chirality: Design and Asymmetric Synthesis. Molecules, 29(10). https://doi.org/10.3390/molecules29102274
dc.identifier.urihttps://doi.org/10.3390/molecules29102274
dc.identifier.urihttps://hdl.handle.net/2346/98711
dc.language.isoeng
dc.subjectatropisomerism
dc.subjectN-sulfinylimine
dc.subjectorientational chirality
dc.subjectSonogashira coupling
dc.titleC(sp)-C(sp) Lever-Based Targets of Orientational Chirality: Design and Asymmetric Synthesis
dc.typeArticle

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