A new selective cleavage of N,N-dicarbamoyl-protected amines using lithium bromide
A new selective cleavage of N,N-dicarbamoyl-protected amines using lithium bromide
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DOI：
10.1021/jo026300b
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发表时间：
2003-02-07
影响因子：
3.6
通讯作者：
Martín, VS
中科院分区：
文献类型：
--
作者：
Hernández, JN;Ramírez, MA;Martín, VS
本文介绍了一种温和的、新的选择性裂解N，N-二氨基甲酰基保护的氨基化合物中的烷氧羰基（Boc，CBz）的方法。该方法基于在乙腈中使用溴化锂，并且与基板中存在的大范围的其他功能兼容。与其他报道的方法相比，该方法特别适用于N，N-Ts，Cbz-双保护胺的Cbz-选择性裂解。一个合理化的从头计算支持的选择性。
A mild and new procedure for the selective cleavage of an alkoxycarbonyl group (Boc, CBz) in N,N-dicarbamoyl-protected amino compounds is described. The method is based on the use of lithium bromide in acetonitrile and is compatible with a large range of other functionalities present in the substrates. Compared with other reported methodologies, the procedure is particularly useful for the Cbz-selective cleavage in N,N-Ts,Cbz-diprotected amines. A rationalization of the selectivity supported by ab initio calculations is also presented.