Electrochemical Corey-Winter reaction. Reduction of thiocarbonates in aqueous methanol media and application to the synthesis of a naturally occurring ?-pyrone.

ABSTRACT: An electrochemical version of the Corey-Winter reaction was developed giving excellent results in aqueous methanol media (MeOH/H₂O (80:20) with AcOH/AcONa buffer 0.5 M as supporting electrolyte), using a reticulated vitreous carbon as cathode in a divided cell. The electrochemical version is much more environmentally friendly than the classical reaction, where a large excess of trialkyl phosphite as reducing agent and high temperatures are required. Thus, cathodic reduction at room temperature of two cyclic thiocarbonates (-1.2 to -1.4 V vs Ag/AgCl) afforded the corresponding alkenes, trans-6-(pent-1-enyl)-?-pyrone and trans-6-(pent-1,4-dienyl)-?-pyrone, which are naturally occurring metabolites isolated from Trichoderma viride and Penicillium, in high chemical yield and with excellent stereo selectivity.

SUBMITTER: Lopez-Lopez EE 

PROVIDER: S-EPMC5852465 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature