Yeung, Charles S.Ziegler, Robert E.Porco, John A.Jacobsen, Eric N.2018-01-252018-01-252014-10-01Charles S Yeung, Robert E Ziegler, John A Porco, Eric N Jacobsen. 2014. "Thiourea-catalyzed enantioselective addition of indoles to pyrones: alkaloid cores with quaternary carbons.." J Am Chem Soc, Volume 136, Issue 39, pp. 13614 - 13617.1520-5126https://hdl.handle.net/2144/26426We 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.13614 - 13617© 2014 American Chemical Society. This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html), which permits copying and redistribution of the article or any adaptations for non-commercial purposes.ChemistryAnion-binding catalysisPictet-Spengler reactionsConcise total synthesisAsymmetric synthesisAlkene cycloadditionC3-quaternary indoleninesCooperative catalysisAlpha-arylationAlkaloidsCatalysisIndolesMolecular structurePyronesStereoisomerismThioureaArticle10.1021/ja508523g