TY - JOUR T1 - Application of 7-azaisatins in enantioselective Morita-Baylis-Hillman reaction. AU - He,Qing, AU - Zhan,Gu, AU - Du,Wei, AU - Chen,Ying-Chun, Y1 - 2016/02/18/ PY - 2015/11/30/received PY - 2016/02/10/accepted PY - 2016/3/16/entrez PY - 2016/3/16/pubmed PY - 2016/3/16/medline KW - 7-azaisatins KW - MBH reaction KW - bifunctional catalysis KW - maleimide KW - β-isocupreidine SP - 309 EP - 13 JF - Beilstein journal of organic chemistry JO - Beilstein J Org Chem VL - 12 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. SN - 1860-5397 UR - https://www.unboundmedicine.com/medline/citation/26977190/Application_of_7_azaisatins_in_enantioselective_Morita_Baylis_Hillman_reaction_ DB - PRIME DP - Unbound Medicine ER -