Proline-based phosphoramidite reagents for the reductive ligation of S-nitrosothiols.

S-Nitrosothiols have many biological implications but are rarely used in organic synthesis. In this work we report the development of proline-based phosphoramidite substrates that can effectively convert S-nitrosothiols to proline-based sulfenamides through a reductive ligation process. A unique property of this method is that the phosphine oxide moiety on the ligation products can be readily removed under acidic conditions. In conjugation with the facile preparation of S-nitrosothiols (RSNO) from the corresponding thiols (RSH), this method provides a new way to prepare proline-based sulfenamides from simple thiol starting materials.

S - 亚硝基硫醇具有许多生物学意义，但在有机合成中很少使用。在这项工作中，我们报道了基于脯氨酸的亚磷酰胺底物的开发，其可通过还原连接过程有效地将S - 亚硝基硫醇转化为基于脯氨酸的次磺酰胺。该方法的一个独特性质是连接产物上的氧化膦部分在酸性条件下可以很容易地除去。结合从相应的硫醇（RSH）简便制备S - 亚硝基硫醇（RSNO），这种方法为从简单的硫醇起始原料制备基于脯氨酸的次磺酰胺提供了一种新途径。