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Organocatalytic Regioselective Concomitant Thiocyanation and Acylation of Oxiranes Using Aroyl Isothiocyanates.

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A regioselective and concomitant transfer of thiocyanate (-SCN) and aroyl/acyl (-COR) groups from aroyl/acyl isothiocyanates onto oxiranes was achieved, giving thiocyanato benzoates in 100% atom economy. In this biomimetic organocatalytic… Click to show full abstract

A regioselective and concomitant transfer of thiocyanate (-SCN) and aroyl/acyl (-COR) groups from aroyl/acyl isothiocyanates onto oxiranes was achieved, giving thiocyanato benzoates in 100% atom economy. In this biomimetic organocatalytic process, one part (-SCN) of aroyl/acyl isothiocyanates acts as the nucleophile whereas the other half (-COR) serves as an electrophilic partner.

Keywords: thiocyanation acylation; organocatalytic regioselective; concomitant thiocyanation; regioselective concomitant; concomitant; aroyl acyl

Journal Title: Organic letters
Year Published: 2017

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