Selective Synthesis of Vinylogous Acyl Sulfonates

Selective Synthesis of Vinylogous Acyl Sulfonates


Vinylogous acyl sulfonates, i.e., sulfonates that are separated from an acyl group by one conjugated C=C bond (example pictured) are useful intermediates in synthetic organic chemistry. They are usually synthesized from 1,3-dicarbonyl compounds using a sulfonate electrophile. However, this reaction gives the products as a mixture of two isomers when the substrate is unsymmetrically substituted.

James K. Tucker and Matthew D. Shair, Harvard University, Cambridge, MA, USA, have developed a regioselective synthesis of vinylogous acyl sulfonates. The team used the corresponding vinyl sulfonates as substrates and performed an allylic oxidation to create the acyl functionality. FeCl3 was used as a catalyst, tert-butyl hydroperoxide (TBHP) as an oxidant, and a mixture of water and acetonitrile as the solvent.

The reaction has a high regioselectivity and gives the desired vinylogous acyl sulfonates in moderate to good yields. The method performs best when there is a quarternary center next to the sulfonate group. The products can be subjected to a variety of further chemical transformations.


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