Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 43, Pages 5884-5888Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202101276
Keywords
alpha-Enolic dithioesters; alpha-Oxoketene N; S-acetals; alpha-Oxoketene S; S-acetals; beta-Ketothioamides; Mitsunobu reaction
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A one-pot protocol was developed for the synthesis of symmetrical and unsymmetrical alpha-oxoketene S,S-/N,S-acetals through chemoselective alkylation of alpha-enolic dithioesters using Mitsunobu chemistry at room temperature. This user-friendly method tolerates a wide range of alcohols and alpha-enolic dithioesters/beta-ketothioamides, providing good yields and highly selective C-S functionalization with E/Z-stereoselectivity.
With unique chemical reactivity, alpha-oxoketene S,S- and N,S-acetals have attracted enormous attention in the past decades, whereas limited reports exist for their synthesis via eco-compatible protocols. Herein, we developed a one-pot protocol for symmetrical and unsymmetrical alpha-oxoketene S,S-/N,S-acetals through chemoselective alkylation of alpha-enolic dithioesters using Mitsunobu chemistry at room temperature. The operationally simple and user-friendly mild protocol tolerates a wide range of alcohols and alpha-enolic dithioesters/beta-ketothioamides. Short reaction time, good yields, highly selective C-S functionalization, and E/Z-stereoselectivity are imperative characteristics of this strategy.
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