Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives.

Author(s) Yamada, T.; Park, K.; Tachikawa, T.; Fujii, A.; Rudolph, M.; Hashmi, S.K.; Sajiki, H.
Journal Org Lett
Date Published 2020 Feb 12

An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals has been developed for the synthesis of indenone derivatives. A wide variety of functionalized indenone derivatives can be obtained in good-to-excellent yields. HMBC and NOESY NMR analyses and mechanistic elucidation experiments revealed that the cyclization occurs via a 1,5-H shift. The cyclic acetal group promoted the 1,5-H shift by activating the benzylic C-H bond and preventing the migration of the alkoxy group by tethering both alkoxy groups.

DOI 10.1021/acs.orglett.0c00221
ISSN 1523-7052
Citation Org Lett. 2020.

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