Literature DB >> 20356104

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

Christoph J Rohbogner1, Stefan Wirth, Paul Knochel.   

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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Year:  2010        PMID: 20356104     DOI: 10.1021/ol100453x

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

Review 1.  An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles.

Authors:  Marcus Baumann; Ian R Baxendale
Journal:  Beilstein J Org Chem       Date:  2013-10-30       Impact factor: 2.883

2.  Directed regioselective ortho,ortho'-magnesiations of aromatics and heterocycles using sBu2Mg in toluene.

Authors:  Andreas Hess; Jan P Prohaska; Sabrina B Doerrich; Florian Trauner; Ferdinand H Lutter; Sébastien Lemaire; Simon Wagschal; Konstantin Karaghiosoff; Paul Knochel
Journal:  Chem Sci       Date:  2021-05-18       Impact factor: 9.825

  2 in total

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