Abstract：An intermediate of chiral amine with 1,3-dioxane structure(4) was obtained by a four-step reaction of condensation, alcoholysis, azidation and reduction, using D-mannitol as material. Three novel chiral thioureas(6a~6c) were synthesized by the reaction of 4 with 3,5-bis(trifluoromethyl)phenyl isothiocyanate, epiquinine isothiocyanate and quinidine isothiocyanate, respectively. The structures were characterized by 1H NMR, 13C NMR, IR and HR-MS. The catalytic performances and selectivities of 6 were investigated by Henry reaction of nitrocarbol with benzaldehyde. The results showed that the yield and enantioselectivity of (S)-2-nitrophenylethan-1-ol were 69% and 78%, respectively, using Et3N as base, toluene as solvent, 5 mol% 6b as catalyst at -30 ℃ for 24 h.
刘秒惜， 王小刚， 何炜， 刘鹏. D-甘露醇衍生的新型手性硫脲的合成及其在Henry反应中的应用[J]. 合成化学, 2016, 24(2): 93-97.
LIU Miao-xi, WANG Xiao-gang, HE Wei, LIU Peng. Synthesis of Novel Chiral Thioureas Derived from D-mannitol and Their Application in Henry Reaction. Chinese Journal of Synthetic Chemistry, 2016, 24(2): 93-97.