A General Method for α-Oxyacylation of Vinyl Ketones Using Koser’s Reagent

Abstract

A direct general method for the preparation of α-oxyacylated vinyl ketones using Koser's hypervalent iodine reagent is reported. A variety of acyloxy groups from long-chain aliphatic, aromatic, α,β-unsaturated carboxylic acids have been installed efficiently for the first time. The oxyacylated adducts were used for the preparation of densely functionalized chiral δ-lactones and cyclopentenes using carbene organocatalysis.

2-Fluoroenones via an Umpolung Morita–Baylis–Hillman Reaction of Enones

“…In 2020, we reported the first umpolung Morita–Baylis–Hillman reaction and showed that it could be used to prepare 1,2-diones and 2-tosylenones. 23d , 25 It occurred to us that this novel concept could be useful for accessing 2-fluoroenones from ubiquitous enones.…”

“…In this context, we and others , have reported extensively on the chemistry of iodine­(III)–enolonium species, i.e., the electrophilic equivalent of classical lithium enolates. In 2020, we reported the first umpolung Morita–Baylis–Hillman reaction and showed that it could be used to prepare 1,2-diones and 2-tosylenones. , It occurred to us that this novel concept could be useful for accessing 2-fluoroenones from ubiquitous enones.…”