Synthesis of [7]Helicene Enantiomers and Exploratory Study of Their Conversion into Helically Chiral Iodoarenes and Iodanes.
asymmetric synthesis
dearomatization
helicenes
iodanes
photocyclization
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
21 Feb 2019
21 Feb 2019
Historique:
received:
19
11
2018
pubmed:
28
12
2018
medline:
28
12
2018
entrez:
28
12
2018
Statut:
ppublish
Résumé
The facile and convenient preparation of both enantiomers of a [7]helicene scaffold from inexpensive (l)-(+)-tartaric acid and 4-methylstyrene is described. These helical structures were transformed into bis-iodinated ether derivatives in order to explore their potential as precursors of novel chiral organoiodane reagents or as iodoarene pre-catalysts. Promising results were obtained in hydroxylative phenol dearomatization/[4+2] cycloaddition cascade and dearomative spirolactonization reactions with encouraging enantiomeric excesses.
Identifiants
pubmed: 30589145
doi: 10.1002/chem.201805761
doi:
Types de publication
Journal Article
Langues
eng
Pagination
2852-2858Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.