3-Deoxy-C-2-formylglycals 80-81與1.1當量的一級胺(包括benzylamine, n-butylamine及n-octylamine)在甲醇的條件下反應十分鐘,可經由Michael加成反應得到3-deoxy-β-enaminals 82-87的產物。3-Deoxy-β-enaminals 82-87的產率為87-95%,伴隨著高度選擇性(E/Z form比率為97:3-98:2)。
β-Enaminals藉由MsCl/pyridine的條件下可合成中等至高產率的C-2-formylglycals,數個問題被深入探討,包括路易士鹼、酸酐(或MsCl)和三號碳及四號碳上取代基之影響。
而β-enaminal與imidazole/PPh3/I2反應亦可合成高產率的C-2-formylglycal。
β-Enaminals同樣可以和SOCl2、I2、TMS/LiBr及Ac2O/d-DMSO進行反應,產生非預期的新化合物。
3-Deoxy-β-enaminals 82-87 that had been prepared by Michael addition of 3-deoxy-C-2-formylglycals 80-81 with 1.1 eguiv of primary amine (including benzylamine, n-butylamine and n-octylamine) in MeOH for 10 minutes. The product, 3-deoxy-β-enaminals 82-87 were abtained in 87-95% with high selectivity (ratio of E/Z: 97:3-98:2).
C-2-Formylglycals were synthesized in medium to good yield by MsCl/pyridine of β-enaminals. Several issues were addressed in depth, including the effect of Lewis bases, acid anhydrides (or MsCl), and the substutient at C3 and C4 position.
C-2-Formylglycal was also synthesized in good yield by treating of β-enaminal with imidazole/PPh3/I2.
β-enaminals were also reacted with SOCl2, I2, TMSCl/LiBr, and Ac2O /d-DMSO to produce unexpected new compounds.