title: Lewis Acid Catalyzed Displacement of Trichloroacetimidates in the Synthesis of Functionalized Pyrroloindolines.
abstract: The pyrroloindoline core is found in many natural products. These structures often differ at the C3a position, which may be substituted with an oxygen, nitrogen, or sp(3)- or sp(2)-hybridized carbon. Utilizing a trichloroacetimidate leaving group, a diversity-oriented approach to these structures has been developed. The trichloroacetimidate intermediate allows for the rapid incorporation of anilines, alcohols, thiols, and carbon nucleophiles. This method was applied in the synthesis of arundinine and a formal synthesis of psychotriasine.
authors.affiliation: Department of Chemistry, Syracuse University , 1-014 Center for Science and Technology, Syracuse, New York 13244, United States.
authors.forename: Arijit A
authors.initials: AA
authors.lastname: Adhikari
authors.affiliation: Department of Chemistry, Syracuse University , 1-014 Center for Science and Technology, Syracuse, New York 13244, United States.
authors.forename: John D
authors.initials: JD
authors.lastname: Chisholm
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D002384:Catalysis; D062845:Chloroacetates / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000081:Acetamides; D062845:Chloroacetates; D058116:Lewis Acids; D011758:Pyrroles; C009528:trichloroacetamide