Synthesis of macrocyclic and medium-sized ring thiolactones via the ring expansion of lactams
Synthesis of macrocyclic and medium-sized ring thiolactones via the ring expansion of lactams
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DOI：
10.1039/d0ob02502j
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发表时间：
2021-02-14
影响因子：
3.2
通讯作者：
Unsworth，William P.
中科院分区：
文献类型：
--
作者：
Palate，Kleopas Y.;Epton，Ryan G.;Unsworth，William P.
报道了一种用于将内酰胺扩环为大环硫代内酯的侧链插入方法，该方法也可以纳入连续扩环（SuRE）序列中。这些反应在热力学上不如类似的内酰胺和内酯形成环扩展过程（这一概念得到了 DFT 数据的支持），但尽管如此，我们还是开发了三种互补的保护基策略来实现这一具有挑战性的转变。
A side chain insertion method for the ring expansion of lactams into macrocyclic thiolactones is reported, that can also be incorporated into Successive Ring Expansion (SuRE) sequences. The reactions are less thermodynamically favourable than the analogous lactam- and lactone-forming ring expansion processes (with this notion supported by DFT data), but nonetheless, three complementary protecting group strategies have been developed to enable this challenging transformation to be achieved.