Morita-Baylis-Hillman Spirannulation under Phosphine- and Anion-Binding Catalysis

Org Lett. 2024 Apr 19;26(15):3273-3278. doi: 10.1021/acs.orglett.4c00847. Epub 2024 Apr 8.

Abstract

We introduce an advancement in Morita-Baylis-Hillman (MBH) chemistry that provides access to α-spirannulated enones. The treatment of enone-tethered azaarenium salts with catalytic amounts of organophosphines provides spiroindenyl dihydropyridines. It represents the α-spirannulation of enones via an intramolecular MBH (IMBH) reaction utilizing dual phosphine- and anion-binding catalysis. The IMBH adducts were subjected to several post-synthetic modifications to access highly functionalized molecules.