Scandium Triflate-Catalyzed Nucleophilic Additions to Indolylmethyl Meldrum’s Acid Derivatives via a Gramine-Type Fragmentation: Synthesis of Substituted Indolemethanes

• Published in: Journal of organic chemistry Vol. 78; no. 20; pp. 10534 - 10540
• Main Authors: Armstrong, Erin L, Grover, Huck K, Kerr, Michael A
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 18.10.2013; Amer Chemical Soc
• Subjects: Catalysis; Chemistry; Chemistry, Organic; Dioxanes - chemistry; Heterocyclic Compounds - chemical synthesis; Heterocyclic Compounds - chemistry; Indoles - chemical synthesis; Indoles - chemistry; Mesylates - chemistry; Molecular Structure; Physical Sciences; Scandium - chemistry; Science & Technology; FUNCTIONALIZATION; 3-ALKYLINDOLES; FRIEDEL-CRAFTS REACTION; BIS(INDOLYL)METHANES; QUATERNARY; INDOLES

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 molecul...