Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 13, Issue -, Pages 2169-2178Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.13.217
Keywords
ball mill; DFT calculations; diketopiperazine; mechanochemistry; pyrrolidine
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Funding
- Centre National de la Recherche Scientifique (CNRS)
- Universite Montpellier
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Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline-proline dipeptides under solvent-free conditions. A deprotection-cyclization sequence yielded the corresponding diketopiperazines that were obtained with a high stereoselectivity which could be explained by DFT calculations. Using this method, an enantiopure disubstituted Pro-Pro diketopiperazine was synthesized in 4 steps, making 5 new bonds using a ball mill.
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