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

Pin-Chun Lin; Zi-Ping Lin; Po-Yen Chen; Min-Tsang Hsieh; Hui-Chang Lin

doi:10.1016/j.carres.2022.108712

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

Carbohydr Res. 2023 Jan:523:108712. doi: 10.1016/j.carres.2022.108712. Epub 2022 Nov 17.

Authors

Pin-Chun Lin¹, Zi-Ping Lin¹, Po-Yen Chen², Min-Tsang Hsieh³, Hui-Chang Lin⁴

Affiliations

¹ Graduate Institute of Pharmaceutical Chemistry, China Medical University, No. 91, Hsueh-Shih Rd., Taichung, 40402, Taiwan.
² School of Pharmacy, China Medical University, No. 91, Hsueh-Shih Rd., Taichung, 40402, Taiwan.
³ School of Pharmacy, China Medical University, No. 91, Hsueh-Shih Rd., Taichung, 40402, Taiwan; Chinese Medicinal Research and Development Center, China Medical University Hospital, No. 2, Yude Rd., Taichung, 40447, Taiwan.
⁴ School of Pharmacy, China Medical University, No. 91, Hsueh-Shih Rd., Taichung, 40402, Taiwan; Graduate Institute of Pharmaceutical Chemistry, China Medical University, No. 91, Hsueh-Shih Rd., Taichung, 40402, Taiwan. Electronic address: lhc550005@yahoo.com.tw.

PMID: 36423508
DOI: 10.1016/j.carres.2022.108712

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.

Keywords: 2-Deoxy-Uloside; 2-Deoxyglycoside; Michael addition; Microwave; β-Enamino ketone.

MeSH terms

Ketones*
Metals
Microwaves*

Substances

Ketones
Metals