Department of Chemistry, University of Bath, Claverton Down, Bath, Somerset, BA2 7AY, UK.
Org Biomol Chem. 2022 Dec 21;21(1):163-168. doi: 10.1039/d2ob01828d.
Heterocyclisation of -butyldimethylsilyl (TBS) protected γ-hydroxy-α,β-unsaturated ketones catalysed by -toluenesulfonic acid (-TSA) to form substituted furans is reported. The reaction proceeds under mild conditions at room temperature in methanol to give a range of furan products (21 examples, up to 98% yield). Mechanistic experiments suggest the reaction proceeds deprotection followed by catalytic dehydrative heterocyclisation.
报道了 - 甲苯磺酸（-TSA）催化 - 叔丁基二甲基硅基（TBS）保护的 γ- 羟基 -α，β- 不饱和酮环化反应生成取代呋喃。该反应在温和条件下，于室温甲醇中进行，得到一系列呋喃产物（21 个例子，最高产率达 98%）。机理实验表明，反应经历了脱保护基和催化脱水杂环化两个步骤。
