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Catalytic Asymmetric [3 + 2] Annulation via Indolyl Copper-Allenylidene Intermediates: Diastereo- and Enantioselective Assembly of Pyrrolo[1,2-a]indoles.

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A catalytic asymmetric decarboxylative [3 + 2] annulation via indolyl copper-allenylidene amphiphilic intermediates has been developed. This protocol offers a straightforward method for the synthesis of biologically important pyrrolo[1,2-a]indoles bearing… Click to show full abstract

A catalytic asymmetric decarboxylative [3 + 2] annulation via indolyl copper-allenylidene amphiphilic intermediates has been developed. This protocol offers a straightforward method for the synthesis of biologically important pyrrolo[1,2-a]indoles bearing contiguous quaternary and tertiary stereogenic centers with excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). In addition, the diversity-oriented synthesis of pyrrolo[1,2-a]indoles was achieved via versatile transformations of the alkyne-containing cycloadducts.

Keywords: pyrrolo; pyrrolo indoles; annulation via; indolyl copper; catalytic asymmetric; via indolyl

Journal Title: Organic letters
Year Published: 2020

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