Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 35, Pages 7793-7797Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403224
Keywords
Organocatalysis; Asymmetric catalysis; Phase-transfer catalysis; Peptidomimetics; Cyclopeptoids
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Funding
- University of Salerno (FARB)
- Italian Ministero dell'Universita e della Ricerca (MIUR) [PRIN 20109Z2XRJ_006]
- People Programme (Marie Curie Actions) of the European Union's Seventh Framework Programme FP7 under REA [PIRSES-GA-2012-319011]
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The first application of cyclopeptoids in asymmetric phase-transfer catalysis was examined. A small library of nine alternating N-substituted-glycine and proline hexacyclopeptoids was tested in the enantioselective alkylation of N-(diphenylmethylene)glycine tert-butyl ester. The presence of an N-arylmethyl side chain in the catalyst was found to be crucial for the synthesis of -amino acids with up to 73%ee.
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