Cooperative N-heterocyclic carbene (NHC)-Lewis acid-mediated regioselective umpolung formal [3 + 2] annulations of alkynyl aldehydes with isatins.
A novel and regioselective umpolung synthesis of spirooxindoles has been developed by cooperative NHC-Lewis acid-mediated formal [3 + 2] annulations of alkynyl aldehydes with isatins. In most cases, the reactions proceeded via a(3)-d(3) umpolung of alkynyl aldehydes resulting in spirooxindole butenolides. In a few cases, spirooxindole furan-3(2H)-ones were formed as the major products via an a(1)-d(1) umpolung process by controlling the reaction temperature. These newly formed spirooxindoles could provide promising candidates for chemical biology and drug lead discovery.
State Key Laboratory of Natural Medicines, Department of Organic Chemistry, China Pharmaceutical University, Nanjing, 210009, P. R. China. lut163@163.com ddmn9999@cpu.edu.cn.
Yu
Y
Zhang
Yingyan
Y
Lu
Weifang
W
Tang
Tao
T
Lu
Ding
D
Du
D000147:Acids, Heterocyclic / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D018360:Crystallography, X-Ray; D007510:Isatin / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D000147:Acids, Heterocyclic; D000447:Aldehydes; D000480:Alkynes; D058116:Lewis Acids; C030011:carbene; D007510:Isatin; D008697:Methane