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Organocatalytic Atroposelective Intramolecular [4+2] Cycloaddition: Synthesis of Axially Chiral Heterobiaryls. 2018
Yidong Liu, and
Xiaoyan Wu, and
Shan Li, and
Lu Xue, and
Chunhui Shan, and
Zhengxing Zhao, and
Hailong Yan
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing, 401331, P. R. China.
The enantioselective construction of axially chiral aryl-naphthopyran skeletons was realized by organocatalytic atroposelective intramolecular [4+2] cycloaddition of in situ generated vinylidene ortho-quinone methides, from 2-ethynylphenol derivatives, with alkynes. Through this method, the heteroatropisomers were obtained with excellent yields and enantioselectivities. Moreover, a speculative model of the stereochemical outcome is proposed based on preliminary mechanistic studies. The products having various functional groups can be easily transformed into valuable intermediates as either potential ligands or organocatalysts.
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