Abstract
In order to provide α-substituted piperazines for early-stage medicinal chemistry studies, a simple, general synthetic approach is required. Here, we report the development of two general and simple procedures for the racemic lithiation/trapping of N-Boc piperazines. Optimum lithiation times have been determined using in situ IR spectroscopy and the previous complicated and diverse literature procedures have been simplified. Subsequent trapping with electrophiles delivered a wide range of α-functionalised N-Boc piperazines. The scope and limitations of the distal N-group has been investigated. The selective α- and β- arylation of N-Boc piperazines via lithiation/Negishi coupling is reported.
Original language | English |
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Pages (from-to) | 7023-7031 |
Number of pages | 9 |
Journal | The Journal of organic chemistry |
Volume | 82 |
Issue number | 13 |
DOIs | |
Publication status | Published - 2 Jun 2017 |
Bibliographical note
© 2017 American Chemical Society. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for detailsKeywords
- Journal Article
Datasets
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General Procedures for the Lithiation/Trapping of N-Boc Piperazines
O'Brien, P. A. (Creator) & Firth, J. (Creator), University of York, 1 Jun 2017
DOI: 10.15124/edbde202-4ed9-4d3f-986b-7ee3bf324fc7
Dataset