Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons
Yeung, Charles S.
Ziegler, Robert E.
Porco, John A.
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CitationYeung, Charles S., Robert E. Ziegler, John A. Porco, and Eric N. Jacobsen. 2014. “Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons.” Journal of the American Chemical Society 136 (39): 13614-13617. doi:10.1021/ja508523g. http://dx.doi.org/10.1021/ja508523g.
AbstractWe 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.
Citable link to this pagehttp://nrs.harvard.edu/urn-3:HUL.InstRepos:22856910
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