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. 2022 Sep 26;61(39):e202209044.
doi: 10.1002/anie.202209044. Epub 2022 Aug 19.

Catalytic Asymmetric α-Alkylsulfenylation with a Disulfide Reagent

Mingying Shi  1 , Qi Zhang  2 , Jiali Gao  1 , Xueling Mi  1 , Sanzhong Luo  2
Affiliations

Catalytic Asymmetric α-Alkylsulfenylation with a Disulfide Reagent

Mingying Shi et al. Angew Chem Int Ed Engl. .

Abstract

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.

Keywords: Alkylsulfenylation; Aminocatalysis; Asymmetric Catalysis; Chiral Primary Amine; Disulfide.

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References

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