Yu Zhang, Yingyan Lu, Weifang Tang, Tao Lu and Ding Du
Org. Biomol. Chem., 2014,12, 3009-3015
DOI:
10.1039/C4OB00145A,
Communication
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 a3–d3 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 a1–d1 umpolung process by controlling the reaction temperature. These newly formed spirooxindoles could provide promising candidates for chemical biology and drug lead discovery.