Telescoped, Divergent, Chemoselective C1 and C1-C1 Homologation of Imine Surrogates: Access to Quaternary Chloro- and Halomethyl-Trifluoromethyl Aziridines.
aziridines
carbenoids
chemoselectivity
homologation
lithium
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
18 02 2019
18 02 2019
Historique:
received:
31
10
2018
pubmed:
15
12
2018
medline:
15
12
2018
entrez:
15
12
2018
Statut:
ppublish
Résumé
A conceptually novel, high-yielding, mono- or bis-homologation was realized with lithium halocarbenoids and enables the one-step, fully chemocontrolled assembly of a new class of quaternary trifluoromethyl aziridines. Trifluoroacetimidoyl chlorides (TFAICs) act as convenient electrophilic platforms, enabling the addition of either one or two homologating elements by simply controlling the stoichiometry of the process. Mechanistic studies highlighted that the homologation event, carried out with two different carbenoids (LiCH
Identifiants
pubmed: 30548145
doi: 10.1002/anie.201812525
pmc: PMC6582437
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
2479-2484Informations de copyright
© 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
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