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
收藏
页码：1416 / 1424
页数：9
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