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. 2016 Aug 8;55(33):9728-32.
doi: 10.1002/anie.201604182. Epub 2016 Jun 27.

Construction of Chiral Tri- and Tetra-Arylmethanes Bearing Quaternary Carbon Centers: Copper-Catalyzed Enantioselective Propargylation of Indoles with Propargylic Esters

Kouhei Tsuchida  1 , Yasushi Senda  1 , Kazunari Nakajima  1 , Yoshiaki Nishibayashi  2
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Construction of Chiral Tri- and Tetra-Arylmethanes Bearing Quaternary Carbon Centers: Copper-Catalyzed Enantioselective Propargylation of Indoles with Propargylic Esters

Kouhei Tsuchida et al. Angew Chem Int Ed Engl. .

Abstract

Copper-catalyzed enantioselective propargylation of indoles with propargylic esters and sequential Huisgen cycloaddition with azides lead to the construction of chiral triarylmethanes, bearing a quaternary carbon center, with high to excellent enantioselectivities. The result described herein can be used in the enantioselective preparation of a tetraarylmethane.

Keywords: alkynes; copper; cycloadditions; enantioselectivity; synthetic methods.

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