Phosphorodiamidate-Directed Metalation of N-Heterocycles using Mg- and Zn-TMP Bases
Organic Letters2010Vol. 12(9), pp. 1984–1987
Citations Over TimeTop 10% of 2010 papers
Abstract
The strong directing ability of the N,N,N',N'-tetramethyldiaminophosphorodiamidate group has been used to achieve selective metalations on various heterocycles such as pyridines, quinolines and quinoxalines with TMP-derived bases like TMPMgCl x LiCl, TMP(2)Mg x 2 LiCl, and TMP(2)Zn x 2 MgCl(2) x 2 LiCl. This protocol was applied in the synthesis of etoricoxib, talnetant and a P-selectin inhibitor.
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