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- Title
Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones.
- Authors
Wang, Yong-Bin; Zheng, Sheng-Cai; Hu, Yu-Mei; Tan, Bin
- 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.
- Publication
Nature Communications, 2017, Vol 8, Issue 5, p15489
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/ncomms15489