Phosphorodiamidate-directed metalation of N-heterocycles using Mg- and Zn-TMP bases

Org Lett. 2010 May 7;12(9):1984-7. doi: 10.1021/ol100453x.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Heterocyclic Compounds / chemistry*
  • Magnesium / chemistry*
  • Metals / chemistry*
  • Phosphorus Compounds / chemistry*
  • Zinc / chemistry*

Substances

  • Heterocyclic Compounds
  • Metals
  • Phosphorus Compounds
  • phosphorodiamidic acid
  • Magnesium
  • Zinc