title: Thiourea-catalyzed enantioselective addition of indoles to pyrones: alkaloid cores with quaternary carbons.
abstract: We report the development of a catalytic method for the enantioselective addition of indoles to pyrone-derived electrophiles. Arylpyrrolidino-derived thioureas catalyze the addition with high stereoselectivity in the presence of catalytic quantities of an achiral Brønsted acid. The indole-pyrone adducts feature a quaternary stereocenter and represent an unusual class of indolines bearing structural resemblance to the hybrid natural product pleiocarpamine.
authors.affiliation: Department of Chemistry and Chemical Biology, Harvard University , 12 Oxford Street, Cambridge, Massachusetts 02138, United States.
authors.forename: Charles S
authors.initials: CS
authors.lastname: Yeung
authors.forename: Robert E
authors.initials: RE
authors.lastname: Ziegler
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
authors.forename: Eric N
authors.initials: EN
authors.lastname: Jacobsen
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D007211:Indoles; D011753:Pyrones; C114765:pleiocarpamine; D013890:Thiourea