A cascade synthesis of S-allyl benzoylcarbamothioates via Mumm-type rearrangement?

Organic & Biomolecular Chemistry Pub Date: 2018-10-09 DOI: 10.1039/C8OB02293C

Abstract

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.

Graphical abstract: A cascade synthesis of S-allyl benzoylcarbamothioates via Mumm-type rearrangement
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