Organocatalytic cycloaddition–elimination cascade for atroposelective construction of heterobiaryls |
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Authors: | Wen-Lei Xu Wei-Ming Zhao Ru-Xia Zhang Jie Chen Ling Zhou |
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Institution: | Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi''an 710102 P. R. China, |
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Abstract: | The first chiral phosphoric acid (CPA) catalyzed cycloaddition–elimination cascade reaction of 2-naphthol- and phenol-derived enecarbamates with azonaphthalenes has been established, providing a highly atroposelective route to an array of axially chiral aryl-C3-benzoindoles in excellent yields with excellent enantioselectivities. The success of this strategy derives from the stepwise process involving CPA-catalyzed asymmetric formal 3 + 2] cycloaddition and subsequent central-to-axial chirality conversion by elimination of a carbamate. In addition, the practicality of this reaction had been verified by varieties of transformations towards functionalized atropisomers.An organocatalytic asymmetric cycloaddition–elimination cascade reaction of aryl enecarbamates with azonaphthalenes has been developed to access axially chiral heterobiaryls in excellent yields and enantioselectivities. |
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