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

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(29)

Опубликована: Май 17, 2023

Sulfondiimines are diaza-analogues of sulfones with a chiral sulfur center. Compared to and sulfoximines, their synthesis transformations have so far been studied lesser extent. Here, we report the enantioselective 1,2-benzothiazine 1-imines, i.e., cyclic sulfondiimine derivatives from sulfondiimines sulfoxonium ylides via C-H alkylation/cyclization reactions. The combination [Ru(p-cymene)Cl2 ]2 newly developed spiro carboxylic acid is key achieving high enantioselectivity.

Язык: Английский

Chiral 3,3,3′,3′-Tetramethyl-1,1′-Spirobiindanyl Cyclopentadienyl (TMSCp) Ligands: Design, Synthesis, and Applications

Organic Letters, Год журнала: 2023, Номер 25(21), С. 3823 - 3828

Опубликована: Май 23, 2023

Chiral cyclopentadienyl (Cp) rhodium(III) are powerful catalysts for achieving asymmetric C–H activation. This paper describes the design and synthesis of a new type chiral Cp ligand bearing 3,3,3′,3′-tetramethyl-1,1′-spirobiindanyl backbone. It features convenient synthesis, easy modification, relatively low cost. Moreover, it holds great potential in activation as exemplified by four examples examined this work.

Язык: Английский

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

Angewandte Chemie, Год журнала: 2023, Номер 135(29)

Опубликована: Май 17, 2023

Abstract Sulfondiimines are diaza‐analogues of sulfones with a chiral sulfur center. Compared to and sulfoximines, their synthesis transformations have so far been studied lesser extent. Here, we report the enantioselective 1,2‐benzothiazine 1‐imines, i.e., cyclic sulfondiimine derivatives from sulfondiimines sulfoxonium ylides via C−H alkylation/cyclization reactions. The combination [Ru( p ‐cymene)Cl 2 ] newly developed spiro carboxylic acid is key achieving high enantioselectivity.

Язык: Английский