Ruthenium(II)/Chiral Carboxylic Acid Catalyzed Enantioselective C–H Functionalization of Sulfoximines

Abstract

Ru(II)-catalyzed enantioselective C–H functionalization reactions of sulfoximines with sulfoxonium ylides are described. The combination of [RuCl2(p-cymene)]2 and a pseudo-C 2-symmetric binaphthyl monocarboxylic acid furnished the S-chiral products in 76:24–92:8 er.

Enantioselective Synthesis of 1,2‐Benzothiazine 1‐Imines via RuII/Chiral Carboxylic Acid‐Catalyzed C−H Alkylation/Cyclization

“…With previous reports on enantioselective C−H alkylation/cyclization reactions of sulfoximines with sulfoxonium ylides by Shi [6d] and our group [6f] in mind, we investigated the reaction of sulfondiimine 1 a and sulfoxonium ylide 2 a using the combination of a metal catalyst and chiral carboxylic acid, which enables carboxylate‐assisted enantioselective C−H activation (Table 1). [11–13] After intensive screening of the reaction conditions, we found that the desired product ( 3 aa ) was obtained in the presence of [Ru( p ‐cymene)Cl 2 ] 2 , AgOTf, and a chiral carboxylic acid ligand.…”

Transition-metal-catalyzed atroposelective synthesis of axially chiral styrenes

“…The fluorescence emission properties of 99d were surveyed, and the indole-derived Weinreb amide 103b could act as a chiral ligand in the Cp*Rh( iii )-catalyzed asymmetric [4+2] annulation of sulfoximine with α-diazo acetyl acetate. 63 Very recently, the construction of axially chiral trisubstituted olefins was also achieved by the same group, which is more challenging in view of their much lower racemization barriers compared with tetrasubstituted alkenes. 64…”

Chiral Brønsted Acid-Catalyzed Kinetic Resolution of Sulfoximines for the Synthesis of Benzothiadiazine-1-Oxides

“…Notably, the desymmetrization strategies require the use of diarylsulfoximine substrates bearing two identical aromatic rings. The development of a catalytic asymmetric reaction with broader substrate scope could achieve diverse synthesis of chiral thiadiazine 1-oxides and thus remains highly desirable.…”