TY - JOUR A1 - He, Qing A1 - Zhan, Gu A1 - Du, Wei A1 - Chen, Ying-Chun T1 - Application of 7-azaisatins in enantioselective Morita–Baylis–Hillman reaction JF - Beilstein Journal of Organic Chemistry PY - 2016/// VL - 12 SP - 309 EP - 313 SN - 1860-5397 DO - 10.3762/bjoc.12.33 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.12.33 KW - 7-azaisatins KW - β-isocupreidine KW - bifunctional catalysis KW - maleimide KW - MBH reaction N2 - 7-Azaisatin and 7-azaoxindole skeletons are valuable building blocks in diverse biologically active substances. Here 7-azaisatins turned out to be more efficient electrophiles than the analogous isatins in the enantioselective Morita–Baylis–Hillman (MBH) reactions with maleimides using a bifunctional tertiary amine, β-isocupreidine (β-ICD), as the catalyst. This route allows a convenient approach to access multifunctional 3-hydroxy-7-aza-2-oxindoles with high enantiopurity (up to 94% ee). Other types of activated alkenes, such as acrylates and acrolein, could also be efficiently utilized. ER -