title: Chemo-, regio-, and enantioselective Pd-catalyzed allylic alkylation of indolocarbazole pro-aglycons.
abstract: [reaction: see text] Monosubstituted isomerically pure indolopyrrolocarbazole precursors have been prepared via palladium-catalyzed asymmetric allylic alkylation methodology, employing both achiral cyclopentenyl electrophiles and chiral glycal derivatives. Chemoselective allylation of (bis)indole lactam pro-aglycon 3 allows access to N-distally substituted indolopyrrolocarbazole derivatives; glyoxamide precursor 14 provides entry into N-proximally substituted derivatives.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Krische
authors.forename: Volker
authors.initials: V
authors.lastname: Berl
authors.forename: Ellen M
authors.initials: EM
authors.lastname: Grenzer
mesh_terms: D000478:Alkylation; D002227:Carbazoles / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002227:Carbazoles; D007211:Indoles; D010165:Palladium