title: H8-BINOL chiral imidodiphosphoric acids catalyzed enantioselective synthesis of dihydroindolo-/-pyrrolo[1,2-a]quinoxalines.
abstract: The first enantioselective synthesis of 5,6-dihydroindolo[1,2-a]quinoxalines is achieved by using a newly developed H8-BINOL-type imidodiphosphoric acid catalyst with low catalyst loading through efficient Pictet-Spengler-type reactions of indolyl anilines with ketones. This methodology also generates phenyl-4,5-dihydropyrrolo[1,2-a]quinoxalines with high yields and excellent enantioselectivities. Moreover, this method was utilized to synthesize an HIV-1 inhibitor with high yield and good enantioselectivity through a one-step procedure.
authors.affiliation: †College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, China.
authors.forename: Yan-Sen
authors.initials: YS
authors.lastname: Fan
authors.affiliation: †College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, China.
authors.forename: Yi-Jun
authors.initials: YJ
authors.lastname: Jiang
authors.affiliation: †College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, China.
authors.forename: Dong
authors.initials: D
authors.lastname: An
authors.affiliation: †College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, China.
authors.forename: Di
authors.initials: D
authors.lastname: Sha
authors.affiliation: ‡Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, CHE205A, Tampa, Florida 33620, United States.
authors.forename: Jon C
authors.initials: JC
authors.lastname: Antilla
authors.affiliation: †College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun 130012, China.
authors.forename: Suoqin
authors.initials: S
authors.lastname: Zhang
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D004164:Diphosphonates / Q000737:chemistry*; D015497:HIV-1 / Q000187:drug effects*; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D019380:Anti-HIV Agents; C406944:BINOL, naphthol; D004164:Diphosphonates; D007659:Ketones; D009284:Naphthols; D011758:Pyrroles; D011810:Quinoxalines; C016514:imidodiphosphonic acid