Enantioselective fluorination of α-chloro-β-keto phosphonates in the presence of chiral palladium complexes

Advances in Catalytic Enantioselective Fluorination, Mono-, Di-, and Trifluoromethylation, and Trifluoromethylthiolation Reactions

“…Kim and co-workers also developed enantioselective fluorination of α-chloro-β-keto phosphonates 22 catalyzed by chiral palladium complex 19c , which gave the corresponding α-chloro-fluoro-β-keto phosphonates 23 with excellent enantioselectivity (up to 95% ee) (Scheme 6 ). 15 …”

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

“…In 2013, Kim’s group [46] described an enantioselective electrophilic fluorination of α-chloro-β-keto phosphonates with up to 95% ee (Scheme 10). Notably, this reaction used an air and moisture-stable chiral palladium complex as the catalyst, which worked well at low catalyst loading (as low as 0.5 mol %).…”

Asymmetric Michael Addition of Pyrazolones to β,γ‐Unsaturated α‐Keto Esters Catalyzed by Binaphthyl‐modified Thiourea

“…In the framework of our research program for the development of synthetic methods for the formation of CC bonds, we recently reported asymmetric Michael addition reaction of various nucleophiles using chiral catalysts . Herein, we report the asymmetric Michael addition of pyrazolones to β,γ‐unsaturated α‐keto esters promoted by binaphthyl‐modified thiourea organocatalyst (Figure ).…”