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Issue 1, 2017
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Diastereo- and enantioselective construction of biologically important pyrrolo[1,2-a]indole scaffolds via catalytic asymmetric [3 + 2] cyclodimerizations of 3-alkyl-2-vinylindoles

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Abstract

A catalytic asymmetric [3 + 2] cyclodimerization of 3-alkyl-2-vinylindoles has been established, which efficiently constructed a pyrrolo[1,2-a]indole scaffold with three contiguous stereogenic centers in a diastereo- and enantioselective fashion (up to 98% yield, >95 : 5 dr, 98 : 2 er). This reaction not only represents the first catalytic asymmetric version of this type of [3 + 2] cyclodimerization, but also supplies important examples for using 2-vinylindoles as nitrogen–carbon–carbon (NCC) building blocks in asymmetric catalysis and synthesis. More importantly, this reaction also provides an efficient method for enantioselectively constructing biologically significant pyrrolo[1,2-a]indole scaffolds.

Graphical abstract: Diastereo- and enantioselective construction of biologically important pyrrolo[1,2-a]indole scaffolds via catalytic asymmetric [3 + 2] cyclodimerizations of 3-alkyl-2-vinylindoles

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Publication details

The article was received on 08 Aug 2016, accepted on 14 Oct 2016 and first published on 19 Oct 2016


Article type: Research Article
DOI: 10.1039/C6QO00446F
Citation: Org. Chem. Front., 2017,4, 57-68
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    Diastereo- and enantioselective construction of biologically important pyrrolo[1,2-a]indole scaffolds via catalytic asymmetric [3 + 2] cyclodimerizations of 3-alkyl-2-vinylindoles

    Z. Zhu, L. Yin, Y. Wang, Y. Shen, C. Li, G. Mei and F. Shi, Org. Chem. Front., 2017, 4, 57
    DOI: 10.1039/C6QO00446F

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