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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.