Hex-1-en-3-one 可藉由D-glucals或D-galactals經過氧化反應而得到，接著再與3當量的一級胺（包括芐胺、正丁胺及正辛胺）在甲醇為溶媒的條件下進行Michael加成反應而得到高產率（87-95%）及高立體選擇性（Z型）的β-enamino ketone 26。
以β-enamino ketone 26為基本骨架與正己醇為基本條件下進行反應，使用數種三當量不同路易士酸，以及溶媒和對溫度進行測試。發現反應在3當量的12N鹽酸，使用100 W/60oC 反應10分鐘，可得到具有高產率（88%）及高位向選擇性（α/β 95/5）之n-hexyl-2-deoxy-α-deoxyulosides(27)。
β-enamino ketone使用3當量鹽酸和氧-及硫-親核試劑在微波反應可得到高產率的α-2-Deoxyglycosides，這個醣加成反應經過二次Michael加成反應，並且在10分鐘內完全反應完畢，及具有高α位向選擇性，產率介於51-93%。
β-enamino ketone溶於DMF中和五當量的碳酸氫鈉、一當量的四丁基溴化胺及0.5當量的醋酸鈀，在室溫下反應三小時，可得鈀的錯化物。
Hex-1-en-3-one that had been prepared by oxidation reactions of D-glucals or D-galactals were subjected to Michael addition15 with 3.0 equiv of primary amines (including benzylamine, n-butylamine, and n-octylamine) in MeOH for 2 h. The products,β-Enamino ketone 26, were obtained in 87-95% with high diastereoselective Z-geometry due to the intramolecular hydrogen bonding.
β-Enamino kentone 26a reacted with n-hexanol under basic conditions. Several Lewis acids (3.0 equiv), solvents and temperatures were examined. Among these reaction shown that 12N HCl (3.0 equiv) at 100 W/60 oC for 10 min was found to provide the desired product n-hexyl-2-deoxy-α-deoxyulosides (27) with the highest isolated yield (88%) and stereoselectivity (ratio of α/β-amomers: 95/5).
α-2-Deoxyglycosides were synthesized in good yields by microware-assisted reaction of β-enamino ketone with various O- and S-nucleophiles in the presence of 3.0 equiv of hydrogen chloride. These glycosyl additions were throgh the double Michael reaction and occurred high α-stereoselectivity and were complete in 10 min in 51-93% yield.
The palladium complex were synthesized in good yields by reacting β-enamino ketone with palladium(II) acetate in the presence of 5.0 equiv of sodium bicarbonate and 1.0 equiv of tetrabutylamino bromide in DMF at room temperature for 3 h.
