Efficient Synthesis of Cyclic Sulfoximines from N‐Propargylsulfinamides through Sulfur–Carbon Bond Formation

• Published in: Chemistry : a European journal Vol. 25; no. 69; pp. 15755 - 15758
• Main Authors: Aota, Yusuke, Maeda, Yoshiaki, Kano, Taichi, Maruoka, Keiji
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 10.12.2019; Wiley Subscription Services, Inc
• Subjects: alkynes; Asymmetric synthesis; Bonding; Carbon; Carbon cycle; Catalysts; Chemical bonds; Chemistry; Chemistry, Multidisciplinary; cyclization; Organic chemistry; Physical Sciences; Science & Technology; sulfinamides; sulfoximines; Sulfur; sulfur heterocycles; NITRENE TRANSFER; sulfoximines; ASYMMETRIC-SYNTHESIS; sulfinamides; SULFIDES; alkynes; sulfur heterocycles; STEREOCHEMISTRY; cyclization; TERT-BUTANESULFINAMIDES; REARRANGEMENT; SULFOXIDES; INTRAMOLECULAR CYCLIZATION; DERIVATIVES; RHODIUM-CATALYZED IMINATION
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201904501

Cyclic sulfoximines were readily synthesized by the cyclization of N‐propargylsulfinamides without using expensive and toxic metal catalysts. This cyclization proceeded without loss of optical purity of chiral sulfinamides through the unusual sulfur–carbon bond formation promoted by an inexpensive inorganic base. This stereospecific cyclization offers a general approach to the asymmetric synthesis of chiral cyclic sulfoximines as an emerging heterocycle in medicinal chemistry. Cyclic sulfoximines were synthesized by the cyclization of readily available N‐propargylsulfinamides under basic conditions without using a metal catalyst. This cyclization proceeded without loss of optical purity of chiral sulfinamides through the unusual sulfur–carbon bond formation promoted by an inexpensive inorganic base.