Synthesis of Chiral Aziridines from Glycals: Application in the Synthesis of a Piperidine-Azepine Fused Derivative

被引：6

作者：

Thakur, Rima ^{[1
]}

Rawal, Girish K. ^{[1
]}

Vankar, Yashwant D. ^{[1
]}

机构：

[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 29期

关键词：

Carbohydrates; Glycals; Aziridines; Chiral pool; Nitrogen heterocycles; RING-OPENING REACTIONS; CERIC AMMONIUM-NITRATE; ONE-POT SYNTHESIS; GLYCOSIDASE INHIBITORS; D-GLUCOSE; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; N-TOSYLAZIRIDINES; HYBRID SUGARS;

D O I：

10.1002/ejoc.201700624

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vicinal chloroamines derived from glycals have been converted into the corresponding chiral aziridines. Although the formation of a tetrahydrofuran derivative is also possible, reaction conditions were developed to give the azirdines exclusively. One of the aziridines is closely related to a compound used in the synthesis of an advanced intermediate en route to Zanamivir, an antiviral agent. Furthermore, one of the aziridines was converted into a piperidine-azepine fused derivative.

引用

页码：4235 / 4241

页数：7

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