Facile Access to Optically Active 2,6-Dialkyl-1,5-Diazacyclooctanes.
[4+4] cycloaddition
asymmetric synthesis
chiral amines
diazacyclooctane
saturated heterocycles
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
18 Nov 2019
18 Nov 2019
Historique:
received:
09
07
2019
revised:
01
08
2019
pubmed:
6
8
2019
medline:
6
8
2019
entrez:
6
8
2019
Statut:
ppublish
Résumé
The chiral substituted 1,5-diazacyclooctane (1,5-DACO) is of considerable importance and has attracted attention from a wide range of fields due to their unique chemical and biological properties. Despite the application potential, further study has not been optimized due to difficulties in their synthetic accessibility. Here, we report that the 1,5-DACO bearing a chiral auxiliary obtained from the formal [4+4] cycloaddition of N-alkyl-α,β-unsaturated imines can be further derivatized by nucleophilic alkylation to give various chiral substituted 1,5-DACO derivatives. The removal of the chiral auxiliary was effectively carried out using hydrogenation over Pearlman's catalyst. This methodology allows the production of a broad range of unprecedented optically active 2,6-dialkyl-1,5-DACO, which could not be accessed by other methods.
Identifiants
pubmed: 31381243
doi: 10.1002/asia.201900938
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
4048-4054Subventions
Organisme : Japan Society for the Promotion of Science
ID : JP15H05843
Organisme : Japan Society for the Promotion of Science
ID : JP18K19154
Organisme : Japan Society for the Promotion of Science
ID : JP18K14341
Organisme : Russian Government Program of Competitive Growth of Kazan Federal University
ID : 4.1493.2017/4.6
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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