Brønsted acid-catalysed enantioselective construction of axially chiral arylquinazolinones

Nature Communications
Yong-Bin WangBin Tan

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.

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Citations

Oct 6, 2017·Chemistry : a European Journal·Jérémy MeradGéraldine Masson
Dec 20, 2017·Nature Chemistry·Liang-Wen QiBin Tan
Jan 27, 2021·Chemical Society Reviews·Bo HanJun-Long Li
Oct 20, 2020·Chemistry : a European Journal·Vinzenz Thönnißen, Frederic W Patureau
Mar 30, 2021·Chemical Reviews·Jun Kee ChengBin Tan
Jun 11, 2019·Organic Letters·You-Dong ShaoDao-Juan Cheng
Dec 27, 2019·The Journal of Organic Chemistry·Shaofeng WuYongbo Zhou
Feb 9, 2018·Accounts of Chemical Research·Yong-Bin Wang, Bin Tan
Dec 10, 2020·The Journal of Organic Chemistry·Erina NiijimaOsamu Kitagawa

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Methods Mentioned

BETA
X-ray
amidation
column chromatography
NMR

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