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

被引：20

作者：

Doherty, William ^{[1
]}

Evans, Paul ^{[1
]}

机构：

[1] Univ Coll Dublin, Sch Chem, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 04期

关键词：

ASYMMETRIC ALPHA-AMINOXYLATION; HYDROXY ALPHA; BETA-UNSATURATED SULFONES; Z-UNSATURATED ESTERS; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ALLYLIC ALCOHOLS; ETHYL (DIARYLPHOSPHONO)ACETATES; SUBSTITUTION-REACTIONS; SELECTIVE SYNTHESIS; KINETIC RESOLUTION;

D O I：

10.1021/acs.joc.5b02556

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An operationally simple protocol for the synthesis of gamma-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 gamma-azido vinyl sulfones, and azide-alkyne click chemistry enabled the synthesis of vinyl sulfone-based triazoles as potential nonpeptidic cysteine protease inhibitors.

引用

页码：1416 / 1424

页数：9

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