[2 + 2] Cycloaddition of Ynamides to Construct 3-Aminocyclobutenones

Org Lett. 2022 Jul 22;24(28):5056-5061. doi: 10.1021/acs.orglett.2c01825. Epub 2022 Jul 11.

Abstract

An efficient Tf2NH-catalyzed [2 + 2] cycloaddition of ynamides under mild conditions has been developed. Within short reaction times, various ynamides are transformed into the corresponding 3-aminocyclobutenones in good to excellent yields. This is the first example for the metal-free intermolecular [2 + 2] self-cycloaddition of ynamides. Meanwhile, the desired cycloaddition products can be easily transformed into aminonaphthol derivatives.