Construction of substituited cyclohexanones through Michael additions to ketosulfoxonium ylides

In this work, a new method for the synthesis of cyclic ketosulfoxonium ylides, containing a tetra-substituted cyclohexanone moiety, is described. These new carbocycles were obtained in an one-pot reaction through two sequential Michael additions from α,β-unsaturated ketosulfoxonium ylides, employing various carbon nucleophiles containing electron-withdrawing groups. Products were obtained in yields up to 75% and as single diastereomer. The main results are presented in the graphical abstract.

The cyclic ylides obteined could be functionalized, delivering substituited 6-membered carbocycles. The O-alkylation of structure 1 could furnish the cyclic vinyl sulfoxide 2. The α-hydroxy cycloexenone 3 can also be obteined starting from 1, as well as the vinyl sulfide 4, under the same reaction condition. The abstence or presence of DMSO can favour the formation of 3 or 4 respectively.

Given the significance of these compounds and their synthetic versatility , ongoing efforts are focused on accessing and expanding this family of derivatives.