1381776-00-6Relevant articles and documents
Efficient C-3 functionalization of 4-dimethylaminopyridine (DMAP). A straightforward access to new chiral nucleophilic catalysts
Poisson, Thomas,Oudeyer, Sylvain,Levacher, Vincent
, p. 3284 - 3287 (2012)
Herein, the straightforward C-3 functionalization of 4- dimethylaminopyridine (DMAP) backbone is disclosed. An efficient halogen-metal exchange procedure from 3-bromo DMAP 1 is reported providing a large panel of C-3 functionalized DMAPs. In addition, a Pd-catalysed C-N cross-coupling reaction is also described furnishing new 3-amino DMAPs. These new functionalization pathways led to the resolution-free synthesis of three new chiral DMAP catalysts in few steps and a good overall yield. These new catalysts were evaluated into the Steglich rearrangement giving modest enantioselectivities (up to 20% ee).