Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives
Tsuyoshi Yamada*, Kwihwan Park, Takumu Tachikawa, Akiko Fujii, Matthias Rudolph, A. Stephen K. Hashmi and Hironao Sajiki*
*Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan,
Email: yamada
gifu-pu.ac.jp, sajikigifu-pu.ac.jp
T. Yamada, K. Park, T. Tachikawa, A. Fujii, M. Rudoplf, A. S. K. Hashmi, H. Sajiki, Org. Lett., 2020, 22, 1883-1888.
DOI: 10.1021/acs.orglett.0c00221
see article for more reactions
Abstract
An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals enables the synthesis of or a broad range of indenone derivatives in very good yields. The cyclic acetal group promotes a 1,5-H shift by activating the benzylic C-H bond and preventing the migration of the alkoxy group by tethering both alkoxy groups.
see article for more examples
Key Words
ID: J54-Y2020
