Phosphorodiamidate-directed metalation of N-heterocycles using Mg- and Zn-TMP bases.
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.
Rohbogner
Christoph J
CJ
Department Chemie, Ludwig-Maximilans Universität München, Butenandtstr. 5-13, 81377 München, Germany.
Wirth
Stefan
S
Knochel
Paul
P
D006571:Heterocyclic Compounds / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D017553:Phosphorus Compounds / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
D006571:Heterocyclic Compounds; D008670:Metals; D017553:Phosphorus Compounds; C436301:phosphorodiamidic acid; D008274:Magnesium; D015032:Zinc