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Enantioselective construction of tricyclic pyrrolidine-fused benzo[b]thiophene 1,1-dioxide derivatives via copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition

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Abstract

A highly efficient copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with benzo[b]thiophene 1,1-dioxides as the dipolarophiles was developed, providing elegant access to novel chiral tricyclic pyrrolidine-fused benzo[b]thiophene 1,1-dioxide derivatives in good to excellent yields (up to 99%) with excellent diastereo- and enantioselectivities (up to >25 : 1 dr, up to 99% ee). Furthermore, the cycloadducts could be conveniently converted to synthetically important tricyclic pyrrolidine-fused benzo[b]thiophene and tetracyclic oxazolidin-2-one derivatives via simple transformations.

Graphical abstract: Enantioselective construction of tricyclic pyrrolidine-fused benzo[b]thiophene 1,1-dioxide derivatives via copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition

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Publication details

The article was received on 26 Jul 2017, accepted on 28 Aug 2017 and first published on 29 Aug 2017


Article type: Research Article
DOI: 10.1039/C7QO00640C
Citation: Org. Chem. Front., 2017, Advance Article
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    Enantioselective construction of tricyclic pyrrolidine-fused benzo[b]thiophene 1,1-dioxide derivatives via copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition

    H. Deng, F. He, C. Li, W. Yang and W. Deng, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00640C

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