Radical-mediated reduction of the dithiocarbamate group under tin-free conditions

Organic & Biomolecular Chemistry
Claire McMasterRichard S Grainger

Abstract

Reductive desulfurisation of dithiocarbamates is conveniently achieved using H(3)PO(2)-Et(3)N-ACCN in refluxing dioxane. Fused and spirocyclic β-lactams, prepared through 4-exo trig carbamoyl radical cyclisation-dithiocarbamate group transfer reactions, are reduced without fragmentation of the strained 4-membered ring. Diethyl tetraacetyl-d-glucopyranosyl dithiocarbamate is selectively reduced with or without acyloxy group migration depending on reaction conditions and choice of reductant. Deuterium incorporation from D(3)PO(2)-Et(3)N is observed for a system involving a nucleophilic radical intermediate, but not in the case of the electrophilic radical obtained through acyloxy group migration on a glucose derivative.

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Citations

Jun 18, 2015·Organic & Biomolecular Chemistry·Carole GuyonMarc Lemaire
Aug 8, 2018·Angewandte Chemie·Christina G Na, Erik J Alexanian
Sep 14, 2018·Organic & Biomolecular Chemistry·Seyedmorteza Hosseyni, Aliasghar Jarrahpour
Apr 9, 2014·Chemistry : a European Journal·Marie BetouRichard S Grainger
Dec 14, 2017·Beilstein Journal of Organic Chemistry·Azim Ziyaei HalimehjaniPetr Beier
Apr 23, 2021·Organic & Biomolecular Chemistry·Gefei LiShin-Ichiro Shoda
Jul 9, 2014·Chemical Reviews·Erick M Carreira, Thomas C Fessard
Apr 26, 2018·The Journal of Organic Chemistry·Azim Ziyaei HalimehjaniPetr Beier

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