Efficient Synthesis of Thionucleoside Nucleosides via Asymmetric Michael/Aldol Reaction

【作者】 黄可心； 渠桂荣； 郭海明；

【机构】 河南师范大学化学化工学院； 南阳理工学院生物与化学工程学院；

【摘要】 Thionucleosides and their derivatives have attracted considerable attention due to the potential antivirus and antitumor activities.~1 However,the main synthetic approaches are still uneconomical and tedious.This challenge can be considered to be part of our ongoing efforts on the asymmetric synthesis of chiral cyclic nucleosides.~2 Thus,a highly efficient Ni(II)/trisoxazoline-catalyzed asymmetric Michael/Aldol reaction has been developed to synthesize chiral thionucleoside analogues in excellent results (40 examples,up to 93%yield,>99:1 dr and 94%ee).The protocol uses a convenient procedure featuring commercially available catalysts and wide substrate scopes make this methodology potentially useful for organic synthesis.更多还原

【Abstract】 Thionucleosides and their derivatives have attracted considerable attention due to the potential antivirus and antitumor activities.~1 However,the main synthetic approaches are still uneconomical and tedious.This challenge can be considered to be part of our ongoing efforts on the asymmetric synthesis of chiral cyclic nucleosides.~2 Thus,a highly efficient Ni(II)/trisoxazoline-catalyzed asymmetric Michael/Aldol reaction has been developed to synthesize chiral thionucleoside analogues in excellent results (40 examples,up to 93%yield,>99:1 dr and 94%ee).The protocol uses a convenient procedure featuring commercially available catalysts and wide substrate scopes make this methodology potentially useful for organic synthesis.更多还原