Catalytic Asymmetric α‐Alkylsulfenylation with a Disulfide Reagent. Issue 39 (19th August 2022)

• Record Type: Journal Article
• Authors: Shi, Mingying; Zhang, Qi; Gao, Jiali; Mi, Xueling; Luo, Sanzhong
• Is Part Of: Angewandte Chemie international edition. Volume 61:Issue 39(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-08-19
• Subjects: Alkylsulfenylation -- Aminocatalysis -- Asymmetric Catalysis -- Chiral Primary Amine -- Disulfide; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202209044
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : 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.