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

Research output

Abstract

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.

Original languageEnglish
Pages (from-to)5685-5693
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number33
Early online date6 Aug 2019
DOIs
Publication statusPublished - 8 Sep 2019

Fingerprint

Oxadiazoles
Anhydrides
anhydrides
purification
Purification
drugs
chemistry
rings
Drug Discovery

Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

@article{79fe4842816c439faadcccd73e4c4b4e,
title = "Diastereoselective Opening of Bridged Anhydrides by Amidoximes Providing Access to 1,2,4-Oxadiazole/Norborna(e)ne Hybrids",
abstract = "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.",
keywords = "Amidoximes, Diastereomers, Diastereoselectivity, Heterocycles, Tricyclic anhydrides",
author = "Sergey Baykov and Marina Tarasenko and Zelenkov, {Lev E.} and Svetlana Kasatkina and Polina Savko and Anton Shetnev",
year = "2019",
month = "9",
day = "8",
doi = "10.1002/ejoc.201900843",
language = "English",
volume = "2019",
pages = "5685--5693",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "33",

}

TY - JOUR

T1 - Diastereoselective Opening of Bridged Anhydrides by Amidoximes Providing Access to 1,2,4-Oxadiazole/Norborna(e)ne Hybrids

AU - Baykov, Sergey

AU - Tarasenko, Marina

AU - Zelenkov, Lev E.

AU - Kasatkina, Svetlana

AU - Savko, Polina

AU - Shetnev, Anton

PY - 2019/9/8

Y1 - 2019/9/8

N2 - 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.

AB - 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.

KW - Amidoximes

KW - Diastereomers

KW - Diastereoselectivity

KW - Heterocycles

KW - Tricyclic anhydrides

UR - http://www.scopus.com/inward/record.url?scp=85070488619&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201900843

DO - 10.1002/ejoc.201900843

M3 - Article

VL - 2019

SP - 5685

EP - 5693

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 33

ER -