Breaking Report
Catalytic Asymmetric Synthesis of Inherently Chiral Saddle-Shaped Dibenzo[b,f][1,5]diazocines†
Jinmiao Zhou,
Mengyao Tang,
Xiaoyu Yang,
Jinmiao Zhou
School of Physical Science and Technology, ShanghaiTech University, Shanghai, 201210 China
Search for more papers by this authorMengyao Tang
School of Physical Science and Technology, ShanghaiTech University, Shanghai, 201210 China
Search for more papers by this authorCorresponding Author
Xiaoyu Yang
School of Physical Science and Technology, ShanghaiTech University, Shanghai, 201210 China
E-mail: [email protected]Search for more papers by this authorJinmiao Zhou,
Mengyao Tang,
Xiaoyu Yang,
Jinmiao Zhou
School of Physical Science and Technology, ShanghaiTech University, Shanghai, 201210 China
Search for more papers by this authorMengyao Tang
School of Physical Science and Technology, ShanghaiTech University, Shanghai, 201210 China
Search for more papers by this authorCorresponding Author
Xiaoyu Yang
School of Physical Science and Technology, ShanghaiTech University, Shanghai, 201210 China
E-mail: [email protected]Search for more papers by this author†
Dedicated to the Special Issue of Emerging Investigators in 2024.
Comprehensive Summary
Dibenzo[b,f][1,5]diazocines are a class of eight-membered heterocycles, which exhibit unique rigid saddle-shaped structure and possess inherent chirality. In this study, we report a convenient and straightforward method for the catalytic enantioselective synthesis of these unique chiral molecules through chiral phosphoric acid-catalyzed dimerization of 2-acylbenzoisocyanates. Notably, the addition of corresponding 2-acylaniline as the co-catalyst significantly improved the efficiency of these reactions, and a simple phase separation operation resulted in products with excellent enantiopurity. Experimental studies were performed to elucidate the mechanism behind these reactions, leading to the proposal of a plausible reaction mechanism based on the study findings.
Supporting Information
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| cjoc202400243-sup-0001-supinfo.pdfPDF document, 7.1 MB |
Appendix S1: Supporting Information |
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