Consecutive C1‐Homologation / Displacement Strategy for Converting Thiosulfonates into  O,S‐ Oxothioacetals | Zendy

Ielo Laura | Zendy; Pillari Veronica | Zendy; Miele Margherita | Zendy; Holzer Wolfgang | Zendy; Pace Vittorio | Zendy

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Consecutive C1‐Homologation / Displacement Strategy for Converting Thiosulfonates into O,S‐ Oxothioacetals

Author(s) -

Ielo Laura,

Pillari Veronica,

Miele Margherita,

Holzer Wolfgang,

Pace Vittorio

Publication year - 2020

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.202000919

Subject(s) - chemistry , chemoselectivity , electrophile , nucleophile , carbenoid , reagent , sulfur , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , catalysis , rhodium

A conceptually intuitive synthesis of oxothioacetals is reported starting from thiosulfonates as electrophilic sulfur donors. The installation of a reactive CH 2 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.

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