4.8 Article

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

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 33, Pages 9728-9732

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201604182

Keywords

alkynes; copper; cycloadditions; enantioselectivity; synthetic methods

Funding

  1. CREST from JST
  2. JSPS [26288044, 26105708, 15K13687, 15H05798]
  3. MEXT
  4. Grants-in-Aid for Scientific Research [15H05798, 26288044, 26105708, 15K13687] Funding Source: KAKEN

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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.

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