Issue 4, 2024

Copper-catalyzed desymmetric silylative-cyclization of 1,6-diynes for synthesis of spirocyclic compounds

Abstract

Spiro rings such as spirooxindoles and spiroindanones are core skeletons in many pharmaceutically active molecules and natural products. Herein, we developed a copper-catalyzed cascade silylation–cyclization reaction of 1,6-diynes which enabled the rapid construction of silyl-functionalized spirocyclic compounds. A variety of racemic and optically pure spirocyclic oxindole, indanone, quinolinone, and tetralone derivatives were obtained in high yields with excellent enantioselectivities and high stereoselectivities.

Graphical abstract: Copper-catalyzed desymmetric silylative-cyclization of 1,6-diynes for synthesis of spirocyclic compounds

Supplementary files

Article information

Article type
Research Article
Submitted
20 Oct 2023
Accepted
20 Dec 2023
First published
20 Dec 2023

Org. Chem. Front., 2024,11, 1211-1217

Copper-catalyzed desymmetric silylative-cyclization of 1,6-diynes for synthesis of spirocyclic compounds

C. Shan, Z. Wang and Y. Xu, Org. Chem. Front., 2024, 11, 1211 DOI: 10.1039/D3QO01731A

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