New metal-free one-pot synthesis of α-2-deoxy-Ulosides by microwave-assisted double Michael Addition of β-enamino ketones. (January 2023)

• Record Type: Journal Article
• Authors: Lin, Pin-Chun; Lin, Zi-Ping; Chen, Po-Yen; Hsieh, Min-Tsang; Lin, Hui-Chang
• Is Part Of: Carbohydrate research. Volume 523(2023)
• Publication Date: 2023-01
• Subjects: 2-Deoxyglycoside -- 2-Deoxy-Uloside -- β-Enamino ketone -- Michael addition -- Microwave; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2022.108712
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: New metal-free one-pot synthesis of α-2-deoxy-ulosides in moderate to good yields by microwave-assisted double Michael addition of various O -nucleophiles to β-enamino ketones in the presence of 12 N HCl. These glycosyl additions occurred with high α-stereoselectivity and were complete in 10–25 min in 51–93% yield. In addition, high α-stereoselectivity was also observed when S -nucleophiles were examined. Graphical abstract: Image 1