A conceptually intuitive synthesis of oxothioacetals is reported starting from thiosulfonates as electrophilic sulfur donors. The installation of a reactive CH2Cl 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. (Figure presented.).
Consecutive C1-Homologation / Displacement Strategy for Converting Thiosulfonates into O,S-Oxothioacetals / Ielo, L.; Pillari, V.; Miele, M.; Holzer, W.; Pace, V.. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 362:23(2020), pp. 5444-5449. [10.1002/adsc.202000919]
Consecutive C1-Homologation / Displacement Strategy for Converting Thiosulfonates into O,S-Oxothioacetals
Pace V.
2020
Abstract
A conceptually intuitive synthesis of oxothioacetals is reported starting from thiosulfonates as electrophilic sulfur donors. The installation of a reactive CH2Cl 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. (Figure presented.).| File | Dimensione | Formato | |
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