Scandium triflate-catalyzed nucleophilic additions to indolylmethyl Meldrum's acid derivatives via a gramine-type fragmentation: synthesis of substituted indolemethanes.
Treatment of indolylmethyl Meldrum's acids with catalytic scandium triflate and a variety of nucleophiles results in the nucleophilic displacement of the Meldrum's acid moiety via a gramine-type fragmentation. The reaction is useful for the generation of heterocyclic compounds of significant molecular complexity.
Department of Chemistry, The University of Western Ontario , London, Ontario, Canada N6A 5B7.
Erin L
EL
Armstrong
Huck K
HK
Grover
Michael A
MA
Kerr
D002384:Catalysis; D004146:Dioxanes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D012538:Scandium / Q000737:chemistry*
D004146:Dioxanes; D006571:Heterocyclic Compounds; D007211:Indoles; D008698:Mesylates; C436603:scandium triflate; C076489:Meldrum's acid; D012538:Scandium