Thiourea-catalyzed enantioselective addition of indoles to pyrones: alkaloid cores with quaternary carbons
Yeung, Charles S.
Ziegler, Robert E.
Porco, John A.
Jacobsen, Eric N.
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CitationCharles 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.
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.