Catalytic Asymmetric α-Alkylsulfenylation with a Disulfide Reagent.
Alkylsulfenylation
Aminocatalysis
Asymmetric Catalysis
Chiral Primary Amine
Disulfide
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:
26 09 2022
26 09 2022
Historique:
received:
20
06
2022
pubmed:
30
7
2022
medline:
23
9
2022
entrez:
29
7
2022
Statut:
ppublish
Résumé
The use of alkylthio electrophiles in synthesis has remained elusive because of the lack of a suitable reagent that is practical and of excellent enantioselectivity and appropriate reactivity. In this work we introduce a novel alkylthio reagent based on the 2-mercapto-5-methyl-1,3,4-thiadiazole (MMTD) fragment for direct alkylsulfenylation of ketones and aldehydes. It can be readily prepared by the oxidative coupling between thiadiazole and other alkylthio reagents and be combined with chiral primary aminocatalysis. This protocol provides facile access to diverse α-alkylthio quaternary carbon centers with good stereoselectivities.
Identifiants
pubmed: 35906183
doi: 10.1002/anie.202209044
doi:
Substances chimiques
Aldehydes
0
Disulfides
0
Indicators and Reagents
0
Ketones
0
Thiadiazoles
0
Carbon
7440-44-0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202209044Informations de copyright
© 2022 Wiley-VCH GmbH.
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Deposition Numbers 2180595 (for 3 aa-3) contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.