Diastereoselective Opening of Bridged Anhydrides by Amidoximes Providing Access to 1,2,4-Oxadiazole/Norborna(e)ne Hybrids

被引：13

作者：

Baykov, Sergey ^{[1
]}

Tarasenko, Marina ^{[2
]}

Zelenkov, Lev E. ^{[1
]}

Kasatkina, Svetlana ^{[3
]}

Savko, Polina ^{[4
]}

Shetnevi, Anton ^{[4
]}

机构：

[1] St Petersburg State Univ, Inst Chem, 26 Univ Sky Pr, St Petersburg 198504, Russia

[2] Yaroslavl State Tech Univ, 88 Moscowsky Pr, Yaroslavl 150023, Russia

[3] Perm State Univ, Ul Bukireva 15, Perm 614990, Russia

[4] Ushinsky Yaroslavl State Pedag Univ, Pharmaceut Technol Transfer Ctr, 108 Respubl Skaya St, Yaroslavl 150000, Russia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 33期

基金：

俄罗斯基础研究基金会;

关键词：

Diastereoselectivity; Diastereomers; Heterocycles; Tricyclic anhydrides; Amidoximes; ENANTIOSELECTIVE SYNTHESIS; SELECTIVE INHIBITORS; POTENT; DISCOVERY; AGONISTS; DERIVATIVES; NORBORNENES; ACTIVATION; PERIPHERY; DESIGN;

D O I：

10.1002/ejoc.201900843

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A unique example of the one-pot trans-diastereoselective reaction of meso-tricyclic anhydrides is reported. The process involves anhydride ring opening by an amidoxime and the sequential cis- to trans- epimerization/cyclodehydration of the O-acylamidoxime intermediate. The resulted 1,2,4-oxadiazole/norborna(e)ne hybrids are obtained in moderate to good yields and > 95 % diastereomeric excess without any additional purifications. These compounds are interesting not only for drug discovery but for other chemistry-related fields due to the presence of two easily modifiable moieties.

引用

页码：5685 / 5693

页数：9

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