Dichotomous Selectivity in Indium-Mediated Aza-Barbier-Type Allylation of 2-N-Acetyl Glycosyl Sulfinylimines in Brine: Convenient Access to Potent Anti-Influenza Agents

被引：1

作者：

Lin, Long-Zhi ^{[1
]}

Yang, Sheng ^{[1
]}

Liu, Wan-Hsuan ^{[1
]}

Shie, Jiun-Jie ^{[1
]}

机构：

[1] Acad Sinica, Inst Chem, Taipei 11529, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 05期

关键词：

UDP-GALF MIMICS; RING-OPENING REACTIONS; STEREOSELECTIVE-SYNTHESIS; IMINOSUGARS; REACTIVITY; INHIBITORS; REAGENTS; SYSTEMS; IMINES;

D O I：

10.1021/acs.joc.1c02121

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly diastereoselective indium-mediated allylation of 2-N-acetyl glycosyl sulfinylimines in brine under mild reaction conditions is reported. The method allows the achievement of a highly remarkable dichotomous selectivity for substrates, providing a single diastereoisomer of the product in 80-98% yield. With chiral (S)-homoallylic sulfinamide (R-s)-5 and (R-s)-8 formed as key intermediates, two potent anti-influenza agents, zanamivir and zanaphosphor, were synthesized in 50% and 41% overall yields, respectively.

引用

收藏

页码：2324 / 2335

页数：12

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