Thiol-free multicomponent synthesis of non-racemic β-acyloxy thioethers from biocatalytically obtained chiral halohydrins

LOPEZ-VIDAL, M. G; LAVANDERA, I.; BARRA, J. L.; BISOGNO, F. R.

ORGANIC & BIOMOLECULAR CHEMISTRY

ROYAL SOC CHEMISTRY

Lugar: CAMBRIDGE; Año: 2023 vol. 22 p. 1420 - 1425

1477-0520

A novel multicomponent chemoenzymatic strategy for the preparation of enantioenriched β-acyloxythioethers has been developed. This robust methodology employs mild bases, air atmosphere, roomtemperature and avoids the use of foul-smelling thiols. Instead, potassium thioacetate is employed as auniversal sulfur source. This chemoselective strategy tolerates aromatic and aliphatic components anddiverse functional groups. The chirality is enzymatically defined by ADH-catalyzed bioreduction ofα-haloketones delivering an enantioenriched halohydrin which is one of the three components, and theoptical purity remains untouched in the final product. Semipreparative scale multicomponent reactionaffords high yield of the products (up to 96%).