title: N-indolyltriethylborate: a useful reagent for synthesis of C3-quaternary indolenines.
abstract: N-Indolyltriethylborate was found to be a useful reagent for dearomatizing C3-alkylation of 3-substituted indoles with both activated and nonactivated alkyl halides to give C3-quaternary indolenines, pyrroloindolines, furoindoline, and hexahydropyridoindoline under mild reaction conditions. The utility of these reagents was demonstrated in the syntheses of a pyrroloindoline-4-cholestene hybrid and debromoflustramine B.
authors.affiliation: Department of Chemistry, Texas A&M University, College Station, Texas 77843-3255, United States.
authors.forename: Aijun
authors.initials: A
authors.lastname: Lin
authors.forename: Jiong
authors.initials: J
authors.lastname: Yang
authors.forename: Mohamed
authors.initials: M
authors.lastname: Hashim
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001881:Borates; D006574:Heterocyclic Compounds, 2-Ring; D007202:Indicators and Reagents; D007211:Indoles; C090331:debromoflustramine B