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

Anjali Dahiya; Wajid Ali; Tipu Alam; Bhisma K. Patel

doi:10.1039/C8OB02293C

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

Anjali Dahiya,

^a Wajid Ali,

^a Tipu Alam

^a and Bhisma K. Patel

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Indian Institute of Technology Guwahati, Assam, India
E-mail: patel@iitg.ernet.in
Fax: +91-3612690762

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.

This article is part of the themed collections: Synthetic methodology in OBC and Celebrating the RAOBC symposium

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DOI: https://doi.org/10.1039/C8OB02293C
Article type: Communication
Submitted: 17 sept. 2018
Accepted: 08 oct. 2018
First published: 09 oct. 2018

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Org. Biomol. Chem., 2018,16, 7787-7791

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

A. Dahiya, W. Ali, T. Alam and B. K. Patel, Org. Biomol. Chem., 2018, 16, 7787 DOI: 10.1039/C8OB02293C

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Organic & Biomolecular Chemistry

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

Abstract

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

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