Journal
TETRAHEDRON LETTERS
Volume 53, Issue 26, Pages 3284-3287Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.04.068
Keywords
4-Dimethylaminopyridine (DMAP); Halogen-metal exchange reaction; Steglich rearrangement; Buchwald-Hartwig cross-coupling reaction
Categories
Funding
- CNRS
- INSA-Rouen
- University of Rouen
- Region Haute Normandie
- MENRT
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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). (C) 2012 Elsevier Ltd. All rights reserved.
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