Copper-Catalyzed Enantioselective Construction of Tertiary Propargylic Sulfones.
asymmetric synthesis
copper
homogeneous catalysis
propargylic substitution
tertiary sulfones
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 03 2019
18 03 2019
Historique:
received:
14
12
2018
pubmed:
22
1
2019
medline:
22
1
2019
entrez:
22
1
2019
Statut:
ppublish
Résumé
Tertiary propargylic sulfones are of significant importance in organic synthesis and medicinal chemistry, but to date no general asymmetric synthesis approach has been developed. We disclose a versatile copper-catalyzed sulfonylation of propargylic cyclic carbonates using sodium sulfinates that allows the construction of propargylic sulfones featuring elusive quaternary stereocenters. This method provides the first successful example of such an enantioselective propargylic sulfonylation, features high asymmetric induction, wide functional group tolerance, and scalability, and enables attractive product diversification.
Identifiants
pubmed: 30663208
doi: 10.1002/anie.201814242
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
3903-3907Subventions
Organisme : Mineco
ID : CTQ2017-88920-P
Pays : International
Organisme : Agència de Gestió d'Ajuts Universitaris i de Recerca
ID : 2017-SGR-232
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.