Consecutive C1‐Homologation / Displacement Strategy for Converting Thiosulfonates into O,S‐Oxothioacetals,Advanced Synthesis & Catalysis

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Consecutive C1‐Homologation / Displacement Strategy for Converting Thiosulfonates into O,S‐Oxothioacetals
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-08-27 , DOI: 10.1002/adsc.202000919
Laura Ielo ₁ , Veronica Pillari ₁ , Margherita Miele ₁ , Wolfgang Holzer ₁ , Vittorio Pace _{1,

2}

Affiliation

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.

中文翻译：

连续的C1同源/置换策略，可将硫代磺酸盐转化为O，S-氧代乙缩醛

据报道，从硫代磺酸盐作为亲电硫供体开始，概念上直观地合成了氧代硫缩醛。安装具有反应性类胡萝卜素试剂的反应性CH ₂ Cl基序，然后立即用醇性基团[（杂）-芳族，脂族]进行亲核置换，可轻松获得标题化合物。在多功能系统中，始终观察到真正的化学选择性。

更新日期：2020-08-27

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