[3+2]‐Cycloadditions of N‐Cyano Sulfoximines with 1, 3‐Dipoles. Issue 18 (20th April 2020)

• Record Type: Journal Article
• Authors: Krauskopf, Felix; Truong, Khai‐Nghi; Rissanen, Kari; Bolm, Carsten
• Is Part Of: European journal of organic chemistry. Issue 18(2020)
• Page Start: 2761
• Page End: 2765
• Publication Date: 2020-04-20
• Subjects: Betaines -- Cycloaddition -- 1, 3‐Dipole -- Oxadiazole -- Triazole; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000335
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Involving the cyano group of N ‐cyano sulfoximines in [3+2]‐cycloaddition reactions with 1, 3‐dipoles provides practical routes for the construction of 5‐membered heterocycles bearing sulfoximinoyl moieties. An ytterbium‐catalyzed cycloaddition utilizing hydrazonoyl chlorides was developed, as well as a reaction involving imidoyl chlorides proceeding without the aid of a catalyst. Following these protocols, a range of sulfoximines with N ‐1, 2, 4‐triazolyl and N ‐1, 2, 4‐oxadiazolyl substituents was prepared. Abstract : In the present study reports 1, 3‐dipolar cycloaddition reactions starting from easily accessible N ‐cyano sulfoximines. In a straightforward manner, sulfoximines with N ‐1, 2, 4‐triazolyl and N ‐1, 2, 4‐oxadiazolyl substituents are prepared in good yields, While the former reactions require the presence of Yb(OTf)3 in catalytic amounts, the latter proceed metal‐free.