2-Phenyl-tetrahydropyrimidine-4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids
| Autor: | Markus Nahrwold, Hans-Georg Stammler, Anna Penner, Beate Neumann, Norbert Sewald, Arvydas Stoncius |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2009 |
| Předmět: |
Carbamate
Peptidomimetic beta(2)-amino acids medicine.medical_treatment Two step Alkylation stereocentres (SRS) Full Research Paper Benzaldehyde lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry self-regeneration of N N-acetals medicine Side chain Organic chemistry β2-amino acids lcsh:Science N-acetals diastereoselective alkylation ring opening chemistry.chemical_classification Chemistry Organic Chemistry Enantioselective synthesis Amino acid peptidomimetics cyclocondensation self-regeneration of stereocentres (SRS) lcsh:Q |
| Zdroj: | Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Vol 5, Iss 1, p 43 (2009) |
| ISSN: | 1860-5397 |
| Popis: | Novel procedures have been developed to condense benzaldehyde effectively with β-amino acid amides to cyclic benzyl aminals. Double carbamate protection of the heterocycle resulted in fully protected chiral β-alanine derivatives. These serve as universal precursors for the asymmetric synthesis of functionalised β2-amino acids containing acid-labile protected side chains. Diastereoselective alkylation of the tetrahydropyrimidinone is followed by a chemoselective two step degradation of the heterocycle to release the free β2-amino acid. In the course of this study, an L-asparagine derivative was condensed with benzaldehyde and subsequently converted to orthogonally protected (R)-β2-homoaspartate. |
| Databáze: | OpenAIRE |
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