1604677-01-1Relevant articles and documents
Cooperative N-heterocyclic carbene (NHC)-Lewis acid-mediated regioselective umpolung formal [3 + 2] annulations of alkynyl aldehydes with isatins
Zhang, Yu,Lu, Yingyan,Tang, Weifang,Lu, Tao,Du, Ding
, p. 3009 - 3015 (2014/05/06)
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.