Enantioselective Synthesis of Fluorinated Indolizidinone Derivatives.

ABSTRACT: The enantioselective synthesis of fluorinated indolizidinone derivatives has been developed. The process involved an enantioselective intramolecular aza-Michael reaction of conjugated amides bearing a pendant α,β-unsaturated ketone moiety, catalyzed by the (S)-TRIP-derived phosphoric acid, followed by dimethyltitanocene methylenation and ring closing metathesis (RCM). Final indolizidine-derived products comprise a fluorine-containing tetrasubstituted double bond generated by the RCM reaction, which is a challenging task. The whole synthetic sequence took place in acceptable overall yields with excellent enantioselectivities.

SUBMITTER: Escolano M 

PROVIDER: S-EPMC10186376 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature