Catalytic Asymmetric α‐Alkylsulfenylation with a Disulfide Reagent

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 (MMT...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2022-09, Vol.61 (39), p.e202209044-n/a
Main Authors: Shi, Mingying, Zhang, Qi, Gao, Jiali, Mi, Xueling, Luo, Sanzhong
Format: Article
Language:English
Subjects:
Aldehydes
Alkylsulfenylation
Aminocatalysis
Asymmetric Catalysis
Chiral Primary Amine
Disulfide
Enantiomers
Ketones
Reagents
Thiadiazoles
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Summary: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. A disulfide‐based alkylthio transfer reagent was developed for the asymmetric α‐alkylsulfenylation of ketones and aldehydes, showing good activity and stereoselectivity when combined with primary amine organocatalysis.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202209044