Synthesis 2021; 53(10): 1795-1804
DOI: 10.1055/a-1343-9451
paper

Straightforward Route to γ-Sultams via Novel Tandem SN/Michael Addition

Anastasiia Klochkova
,
Andrey Bubyrev
,
Dmitry Dar’in
,
,
,
Viktor Sokolov
This research was supported by the grant of the President of the Russian Federation project no. МK-1073.2020.3.


Abstract

A novel tandem approach to trisubstituted γ-sultams has been developed involving N-alkylation of methanesulfonanilides with EWG-substituted allyl bromides followed by intramolecular Michael addition. A series of various isothiazolidine 1,1-dioxides have been prepared under mild transition-metal-free conditions in high yields and trans-diastereoselectivity (confirmed by X-ray crystallography). The dependence of reactivity on electronic properties of substrates has been investigated.

Supporting Information



Publication History

Received: 04 November 2020

Accepted after revision: 29 December 2020

Publication Date:
29 December 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
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