Aminooxylation Horner-Wadsworth-Emmons Sequence for the Synthesis of Enantioenriched γ-Functionalized Vinyl Sulfones

The Journal of Organic Chemistry
William Doherty, Paul Evans

Abstract

An operationally simple protocol for the synthesis of γ-hydroxy vinyl sulfones has been developed using a proline-based aldehyde aminooxylation, followed by a vinyl sulfone forming Horner-Wadsworth-Emmons olefination. The adducts, formed in high enantiopurity, were subsequently converted to γ-azido vinyl sulfones, and azide-alkyne click chemistry enabled the synthesis of vinyl sulfone-based triazoles as potential nonpeptidic cysteine protease inhibitors.

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Citations

May 21, 2016·Lancet·Ryan Essex
Dec 31, 2016·The Journal of Organic Chemistry·Prakash R Sultane, Christopher W Bielawski
Apr 11, 2019·Organic & Biomolecular Chemistry·Angela S Carlson, Joseph J Topczewski
Jul 17, 2019·The Journal of Organic Chemistry·Xiao LiangYuanjiang Pan
Jun 6, 2018·The Journal of Organic Chemistry·Amy A OttJoseph J Topczewski

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