Organocatalytic atroposelective construction of axially chiral N, N- and N, S-1,2-azoles through novel ring formation approach

Yu Chang, Chuandong Xie, Hong Liu, Shengli Huang, Pengfei Wang, Wenling Qin () and Hailong Yan ()
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Yu Chang: Chongqing University
Chuandong Xie: Chongqing University
Hong Liu: Chongqing University
Shengli Huang: Chongqing University
Pengfei Wang: Chongqing University
Wenling Qin: Chongqing University
Hailong Yan: Chongqing University

Nature Communications, 2022, vol. 13, issue 1, 1-11

Abstract: Abstract 1,2-Azoles are privileged structures in ligand/catalyst design and widely exist in many important natural products and drugs. In this report, two types of axially chiral 1,2-azoles (naphthyl-isothiazole S-oxides with a stereogenic sulfur center and atropoisomeric naphthyl pyrazoles) are synthesized via modified vinylidene ortho-quinone methide intermediates. Diverse products are acquired in satisfying yields and good to excellent enantioselectivities. The vinylidene ortho-quinone methide intermediates bearing two hetero atoms at 5-position have been demonstrated as a platform molecule for the atroposelective synthesis of axially chiral 1,2-azoles. This finding not only enrich our knowledge of vinylidene ortho-quinone methide chemistry but also provide the easy preparation method for diverse atropisomeric heterobiaryls that were inaccessible by existing methodologies. The obtained chiral naphthyl-isothiazole S-oxides and naphthyl-pyrazoles have demonstrated their potential application in further synthetic transformations and therapeutic agents.

Date: 2022
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DOI: 10.1038/s41467-022-29557-1

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