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

Sulfondiimines are diaza‐analogues of sulfones with a chiral sulfur center. Compared to sulfones and sulfoximines, their synthesis and transformations have so far been studied to a lesser extent. Here, we report the enantioselective synthesis of 1,2‐benzothiazine 1‐imines, i.e., cyclic sulfondiimine...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2023-07, Vol.62 (29), p.e202305480-n/a
Main Authors: Huang, Long‐Tao, Kitakawa, Yuta, Yamada, Kodai, Kamiyama, Futa, Kojima, Masahiro, Yoshino, Tatsuhiko, Matsunaga, Shigeki
Format: Article
Language:English
Subjects:
1,2-Benzothiazine 1-Imine
Alkylation
Asymmetric Catalysis
Carboxylic acids
Chemical reactions
Cymene
C−H Activation
Enantiomers
Imines
Ruthenium
Sulfondiimine
Sulfones
Sulfur
Synthesis
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Summary:Sulfondiimines are diaza‐analogues of sulfones with a chiral sulfur center. Compared to sulfones and sulfoximines, their synthesis and transformations have so far been studied to a lesser extent. Here, we report the enantioselective synthesis of 1,2‐benzothiazine 1‐imines, i.e., cyclic sulfondiimine derivatives from sulfondiimines and sulfoxonium ylides via C−H alkylation/cyclization reactions. The combination of [Ru(p‐cymene)Cl2]2 and a newly developed chiral spiro carboxylic acid is key to achieving high enantioselectivity. Enantioselective C−H alkylation/cyclization of sulfondiimines with sulfoxonium ylides using a RuII catalyst and a newly developed chiral spiro carboxylic acid enables the synthesis of 1,2‐benzothiazine 1‐imines, thus expanding the accessible chemical space of chiral hexavalent organosulfur scaffolds relevant to biologically active compounds.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202305480