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Updated: Jul 31, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Enantioselective Synthesis of Fluorinated Indolizidinone Derivatives
Marcos Escolano1, Daniel Gaviña1, Santiago Díaz-Oltra1
1Department of Organic Chemistry, University of Valencia, Avda Vicente Andrés Estellés s/n, 46100 Burjassot, Valencia, Spain.
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.
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