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

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

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 i...

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Veröffentlicht in:Carbohydrate research 2023-01, Vol.523, p.108712-108712, Article 108712
Hauptverfasser: Lin, Pin-Chun, Lin, Zi-Ping, Chen, Po-Yen, Hsieh, Min-Tsang, Lin, Hui-Chang
Format: Artikel
Sprache:eng
Schlagworte:
2-Deoxy-Uloside
2-Deoxyglycoside
carbohydrates
chemical reactions
Ketones
Metals
Michael addition
Microwave
microwave treatment
Microwaves
synthesis
β-Enamino ketone
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Zusammenfassung: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. [Display omitted]
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2022.108712