Asymmetric Synthesis of 2-Arylindolines and 2,2-Disubstituted Indolines by Kinetic Resolution.
asymmetric synthesis
enantioselectivity
heterocycles
kinetic resolution
lithiation
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
11 Aug 2021
11 Aug 2021
Historique:
received:
07
04
2021
pubmed:
11
6
2021
medline:
18
8
2021
entrez:
10
6
2021
Statut:
ppublish
Résumé
Kinetic resolution of 2-arylindolines (2,3-dihydroindoles) was achieved by treatment of their N-tert-butoxycarbonyl (Boc) derivatives with n-butyllithium and sparteine in toluene at -78 °C followed by electrophilic quench. The unreacted starting materials together with the 2,2-disubstituted products could be isolated with high enantiomer ratios. Variable temperature NMR spectroscopy showed that the rate of Boc rotation was fast (ΔG
Identifiants
pubmed: 34110662
doi: 10.1002/chem.202101248
pmc: PMC8456874
doi:
Substances chimiques
Indoles
0
Sparteine
298897D62S
indoline
6DPT9AB2NK
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
11670-11675Subventions
Organisme : Engineering and Physical Sciences Research Council
ID : EP/R024294/1
Informations de copyright
© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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