2-Phenyl-tetrahydropyrimidine-4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids
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 fu...
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Beilstein-Institut
2009-09-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.5.43 |
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doaj-0fbbce44f71e438681c4f89579d49c172021-02-02T01:53:32ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972009-09-01514310.3762/bjoc.5.431860-5397-5-432-Phenyl-tetrahydropyrimidine-4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acidsMarkus Nahrwold0Arvydas Stončius1Anna Penner2Beate Neumann3Hans-Georg Stammler4Norbert Sewald5Bielefeld University, Department of Chemistry, Organic and Bioorganic Chemistry, Universitätsstr. 25, 33615 Bielefeld, GermanyBielefeld University, Department of Chemistry, Organic and Bioorganic Chemistry, Universitätsstr. 25, 33615 Bielefeld, GermanyBielefeld University, Department of Chemistry, Organic and Bioorganic Chemistry, Universitätsstr. 25, 33615 Bielefeld, GermanyBielefeld University, Department of Chemistry, Inorganic Chemistry, Universitätsstr. 25, 33615 Bielefeld, GermanyBielefeld University, Department of Chemistry, Inorganic Chemistry, Universitätsstr. 25, 33615 Bielefeld, GermanyBielefeld University, Department of Chemistry, Organic and Bioorganic Chemistry, Universitätsstr. 25, 33615 Bielefeld, GermanyNovel 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.https://doi.org/10.3762/bjoc.5.43β2-amino acidscyclocondensationdiastereoselective alkylationN,N-acetalspeptidomimeticsring openingself-regeneration of stereocentres (SRS) |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Markus Nahrwold Arvydas Stončius Anna Penner Beate Neumann Hans-Georg Stammler Norbert Sewald |
| spellingShingle |
Markus Nahrwold Arvydas Stončius Anna Penner Beate Neumann Hans-Georg Stammler Norbert Sewald 2-Phenyl-tetrahydropyrimidine-4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids Beilstein Journal of Organic Chemistry β2-amino acids cyclocondensation diastereoselective alkylation N,N-acetals peptidomimetics ring opening self-regeneration of stereocentres (SRS) |
| author_facet |
Markus Nahrwold Arvydas Stončius Anna Penner Beate Neumann Hans-Georg Stammler Norbert Sewald |
| author_sort |
Markus Nahrwold |
| title |
2-Phenyl-tetrahydropyrimidine-4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids |
| title_short |
2-Phenyl-tetrahydropyrimidine-4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids |
| title_full |
2-Phenyl-tetrahydropyrimidine-4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids |
| title_fullStr |
2-Phenyl-tetrahydropyrimidine-4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids |
| title_full_unstemmed |
2-Phenyl-tetrahydropyrimidine-4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids |
| title_sort |
2-phenyl-tetrahydropyrimidine-4(1h)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2009-09-01 |
| description |
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. |
| topic |
β2-amino acids cyclocondensation diastereoselective alkylation N,N-acetals peptidomimetics ring opening self-regeneration of stereocentres (SRS) |
| url |
https://doi.org/10.3762/bjoc.5.43 |
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