Organocatalytic Regioselective Concomitant Thiocyanation and Acylation of Oxiranes Using Aroyl Isothiocyanates

Anju Modi; Wajid Ali; Bhisma K Patel

doi:10.1021/acs.orglett.6b03430

Organocatalytic Regioselective Concomitant Thiocyanation and Acylation of Oxiranes Using Aroyl Isothiocyanates

Org Lett. 2017 Feb 3;19(3):432-435. doi: 10.1021/acs.orglett.6b03430. Epub 2017 Jan 11.

Authors

Anju Modi¹, Wajid Ali¹, Bhisma K Patel¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Guwahati , North Guwahati 781039, India.

PMID: 28075598
DOI: 10.1021/acs.orglett.6b03430

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.

Publication types

Research Support, Non-U.S. Gov't