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Expanding the scope of methyl xanthate esters - From Barton-McCombie reaction auxiliary to versatile protective group
Tetrahedron ( IF 2.1 ) Pub Date : 2017-09-18 , DOI: 10.1016/j.tet.2017.09.022
Karin Thorsheim , Sophie Manner , Ulf Ellervik

The methyl xanthate ester is presented as a versatile protective group for alcohols. Hydroxyl groups can easily be transformed into methyl xanthate esters by several methods and are commonly used as an auxiliary in the Barton-McCombie reaction. We show that these methyl xanthate esters can readily and chemoselectively be cleaved under mild conditions by the action of diethylenetriamine using microwave heating. This method is orthogonal to many common hydroxyl protective groups that can be introduced and cleaved in the presence of methyl xanthate ester.



中文翻译:

扩大黄原酸甲酯的范围-从Barton-McCombie反应助剂到多功能保护基

黄原酸甲酯是醇的通用保护基。羟基可通过几种方法轻松转化为黄原酸甲酯,通常用作Barton-McCombie反应的助剂。我们表明,在微波条件下,利用二亚乙基三胺的作用,在温和的条件下,这些黄原酸酯可以很容易地被化学选择性裂解。该方法与许多常见的羟基保护基团正交,该保护基团可以在黄原酸酯甲酯的存在下引入和裂解。

更新日期:2017-09-18
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