A catalyst and solvent free synthesis of S-allyl benzoylcarbamothioates has been achieved from the in situ generated benzoylcarbonimidothioates obtained by reacting MBH alcohols with aroyl isothiocyanates. An intramolecular thia-Michael addition of the in situ generated adduct triggers a Mumm-type rearrangement leading to a stereoselective synthesis of highly functionalised S-allyl benzoylcarbamothioates.
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A cascade synthesis of S-allyl benzoylcarbamothioates via Mumm-type rearrangement.
Org Biomol Chem
October 2018
Department of Chemistry, Indian Institute of Technology Guwahati, 781 039, Assam, India.
A catalyst and solvent free synthesis of S-allyl benzoylcarbamothioates has been achieved from the in situ generated benzoylcarbonimidothioates obtained by reacting MBH alcohols with aroyl isothiocyanates. An intramolecular thia-Michael addition of the in situ generated adduct triggers a Mumm-type rearrangement leading to a stereoselective synthesis of highly functionalised S-allyl benzoylcarbamothioates.
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