Consecutive C1‐Homologation / Displacement Strategy for Converting Thiosulfonates into O, S‐Oxothioacetals. Issue 23 (6th October 2020)

• Record Type: Journal Article
• Authors: Ielo, Laura; Pillari, Veronica; Miele, Margherita; Holzer, Wolfgang; Pace, Vittorio
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 23(2020)
• Page Start: 5444
• Page End: 5449
• Publication Date: 2020-10-06
• Subjects: Homologation -- Carbenoids -- Oxothioacetals -- Sequential processes -- Sulfur; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202000919
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A conceptually intuitive synthesis of oxothioacetals is reported starting from thiosulfonates as electrophilic sulfur donors. The installation of a reactive CH2 Cl motif with a homologating carbenoid reagent, followed by the immediate nucleophilic displacement with alcoholic groups [(hetero)‐aromatic, aliphatic] offer a convenient access to the title compounds. Genuine chemoselectivity is uniformly observed in the case of multi‐functionalized systems. Abstract :