Comparison of the reactivity of β-thiolactones and β-lactones toward ring-opening by thiols and amines
Comparison of the reactivity of β-thiolactones and β-lactones toward ring-opening by thiols and amines
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DOI：
10.1039/c2ob25640a
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发表时间：
2012-01-01
影响因子：
3.2
通讯作者：
Crich, David
中科院分区：
文献类型：
--
作者：
Noel, Amandine;Delpech, Bernard;Crich, David
报道了简单 β-内酯和 β-硫内酯对硫醇和伯胺的比较反应性的研究。发现简单的3-巯基甲基-2-氧杂环丁酮在碱水溶液存在下发生重排，得到相应的硫杂环丁烷-3-羧酸而不是3-羟甲基-2-硫杂环丁酮。讨论了 β-硫内酯在生物有机和药物化学中的应用。
An investigation into the comparative reactivity of simple beta-lactones and beta-thiolactones toward a thiol and a primary amine is reported. A simple 3-mercaptomethyl-2-oxetanone is found to undergo rearrangement in the presence of aqueous base to give the corresponding thietane-3-carboxylic acid rather than the 3-hydroxymethyl-2-thietanone. Implications for the use of beta-thiolactones in bioorganic and medicinal chemistry are discussed.