Yang Bing, Shen Minxing, Ji Xiaozhou, Xu Ziyan, Sun Hao, Jiang Bo, Li Guigen
Institute of Chemistry and Biomedical Sciences and School of Chemistry and Chemical Engineering, Nanjing University , Nanjing, 210093 China.
Department of Chemistry and Biochemistry, Texas Tech University , Lubbock, Texas 79409-1061, United States.
J Org Chem. 2016 Mar 18;81(6):2488-93. doi: 10.1021/acs.joc.6b00049. Epub 2016 Feb 29.
Seventeen examples of aza-Morita-Baylis-Hillman (aza-MBH) adducts have been synthesized by reacting chiral N-phosphonyl imines with acrylonitrile in good to excellent yields (up to 96%) and high diastereoselectivity (up to 99:1 dr). The synthesis of these adducts followed the method of group-assisted purification (GAP) chemistry, in which the pure aza-MBH products were readily obtained by washing the crude products with cosolvents of hexane and ethyl acetate.
通过使手性N-膦酰基亚胺与丙烯腈反应，已合成出17个氮杂-Morita-Baylis-Hillman（aza-MBH）加合物实例，产率良好至优异（高达96%），非对映选择性高（高达99:1 dr）。这些加合物的合成遵循基团辅助纯化（GAP）化学方法，其中通过用己烷和乙酸乙酯的共溶剂洗涤粗产物，很容易获得纯的aza-MBH产物。
