Asymmetric Allylic Substitution-Isomerization for the Modular Synthesis of Axially Chiral N-Vinylquinazolinones
Jia-Yu Zou
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorYu-Ying Yang
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorJun Gu
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorFei Liu
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorDr. Zhiwen Ye
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorDr. Wenbin Yi
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorCorresponding Author
Prof. Ying He
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorJia-Yu Zou
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorYu-Ying Yang
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorJun Gu
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorFei Liu
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorDr. Zhiwen Ye
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorDr. Wenbin Yi
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorCorresponding Author
Prof. Ying He
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing, 210094 China
Search for more papers by this authorAbstract
Axially chiral N-substituted quinazolinones are important bioactive molecules, which are presented in many synthetic drugs. However, most strategies toward their atroposelective synthesis are mainly limited to the axially chiral arylquinazolinone frameworks. The development of modular synthetic methods to access diverse quinazolinone-based atropisomers remains scarce and challenging. Herein, we report the regio- and atroposelective synthesis of axially chiral N-vinylquinazolinones via the strategy of asymmetric allylic substitution-isomerization. The catalysis system utilized both asymmetric transition-metal catalysis and organocatalysis to efficiently afford trisubstituted and tetrasubstituted N-vinylquinazolinone atropisomers, respectively. With the meticulous design of β-substituted allylic substrates, both Z- and E-tetrasubstituted axially chiral N-vinylquinazolinones were obtained in good yields and high enantioselectivities.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
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