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.

SUBMITTER: Yeung CS 

PROVIDER: S-EPMC4235369 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature