In/I2 mediated functional group transformation: a direct approach toward the selective conversion of dithioester to ester

Abstract

A facile, direct approach for the selective conversion of dithioester to ester functional group has been developed. In/I2 in methanol efficiently promotes the interesting functional group transformation at room temperature. Applying the newly developed mild conditions, a series of α-allyl-β′-oxodithioesters have been converted to the corresponding α-allyl-β′-oxoesters in moderate to good yields. Interestingly, during the transformation the dithioester groups of the starting α-allyl-β′-oxodithioesters are selectively transformed to the corresponding methyl esters while the other functionalities within the moiety remained unaffected; hence requires no cumbersome protection–deprotection during the synthetic transformation.