Synthesis of α-2-deoxy-ulosides by Michael addition of hex-1-en-3-ones

α-2-Deoxyulosides were synthesized in moderate to good yields by Michael addition of various O-nucleophiles to hex-1-en-3-ones in the presence of NaOH. These glycosyl additions were complete in 30 min at room temperature with high α-stereoselectivity in 53-92% yield. In addition, high α-stereoselectivity was also observed when S-nucleophiles were examined at 0 °C for 90 min.

Graphical abstractDownload full-size image