Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones

Yong-Bin Wang, Sheng-Cai Zheng, Yu-Mei Hu and Bin Tan ()
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Yong-Bin Wang: South University of Science and Technology of China
Sheng-Cai Zheng: South University of Science and Technology of China
Yu-Mei Hu: South University of Science and Technology of China
Bin Tan: South University of Science and Technology of China

Nature Communications, 2017, vol. 8, issue 1, 1-9

Abstract: Abstract The axially chiral arylquinazolinone acts as a privileged structural scaffold, which is present in a large number of natural products and biologically active compounds as well as in chiral ligands. However, a direct catalytic enantioselective approach to access optically pure arylquinazolinones has been underexplored. Here we show a general and efficient approach to access enantiomerically pure arylquinazolinones in one-pot fashion catalysed by chiral phosphoric acids. A variety of axially chiral arylquinazolinones were obtained in high yields with good to excellent enantioselectivities under mild condition. Furthermore, we disclosed a method for atroposelective synthesis of alkyl-substituted arylquinazolinones involving Brønsted acid-catalysed carbon–carbon bond cleavage strategy. Finally, the asymmetric total synthesis of eupolyphagin bearing a cyclic arylquinazolinone skeleton was accomplished with an overall yield of 32% in six steps by utilizing the aforementioned methodology.

Date: 2017
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DOI: 10.1038/ncomms15489

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