Lewis acid-catalysed nucleophilic opening of a bicyclic hemiaminal followed by ring contraction: Access to functionalized L-idonojirimycin derivatives.
Bicycle opening
Hemiaminal
Iminosugar
Skeletal rearrangement
Journal
Carbohydrate research
ISSN: 1873-426X
Titre abrégé: Carbohydr Res
Pays: Netherlands
ID NLM: 0043535
Informations de publication
Date de publication:
15 Jan 2019
15 Jan 2019
Historique:
received:
31
10
2018
revised:
12
11
2018
accepted:
12
11
2018
pubmed:
30
11
2018
medline:
5
6
2019
entrez:
30
11
2018
Statut:
ppublish
Résumé
The Lewis acid-catalyzed nucleophilic opening of a D-gluco-configured bicyclic hemiaminal has been examined. Several Lewis acids and silylated nucleophiles have been screened allowing the introduction of acetophenone, phosphonate or nitrile at the pseudoanomeric position in satisfactory yields and high 1,2 trans stereoselectivities. Their skeletal rearrangement triggered by the N-benzyl anchimeric assistance provided the corresponding L-ido-configured piperidines displaying various functional groups at C-6 position in good yield.
Identifiants
pubmed: 30496874
pii: S0008-6215(18)30639-6
doi: 10.1016/j.carres.2018.11.008
pii:
doi:
Substances chimiques
Bridged Bicyclo Compounds, Heterocyclic
0
Imino Sugars
0
Lewis Acids
0
Piperidines
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
65-71Informations de copyright
Copyright © 2018 Elsevier Ltd. All rights reserved.