2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids
Nahrwold M, Stoncius A, Penner A, Neumann B, Stammler H-G, Sewald N (2009)
Beilstein Journal of Organic Chemistry 5(43).
Zeitschriftenaufsatz
| Veröffentlicht | Englisch
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Autor*in
Nahrwold, Markus;
Stoncius, Arvydas;
Penner, Anna;
Neumann, BeateUniBi;
Stammler, Hans-GeorgUniBi;
Sewald, NorbertUniBi 
Einrichtung
Abstract / Bemerkung
Novel procedures have been developed to condense benzaldehyde effectively with beta-amino acid amides to cyclic benzyl aminals. Double carbamate protection of the heterocycle resulted in fully protected chiral beta-alanine derivatives. These serve as universal precursors for the asymmetric synthesis of functionalised beta(2)-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 beta(2)-amino acid. In the course of this study, an L-asparagine derivative was condensed with benzaldehyde and subsequently converted to orthogonally protected (R)-beta(2)-homoaspartate.
Stichworte
ring opening;
peptidomimetics;
stereocentres (SRS);
self-regeneration of;
cyclocondensation;
diastereoselective alkylation;
beta(2)-amino acids;
N;
N-acetals
Erscheinungsjahr
2009
Zeitschriftentitel
Beilstein Journal of Organic Chemistry
Band
5
Ausgabe
43
Urheberrecht / Lizenzen
eISSN
1860-5397
Page URI
https://pub.uni-bielefeld.de/record/1590600
Zitieren
Nahrwold M, Stoncius A, Penner A, Neumann B, Stammler H-G, Sewald N. 2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids. Beilstein Journal of Organic Chemistry. 2009;5(43).
Nahrwold, M., Stoncius, A., Penner, A., Neumann, B., Stammler, H. - G., & Sewald, N. (2009). 2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids. Beilstein Journal of Organic Chemistry, 5(43). https://doi.org/10.3762/bjoc.5.43
Nahrwold, Markus, Stoncius, Arvydas, Penner, Anna, Neumann, Beate, Stammler, Hans-Georg, and Sewald, Norbert. 2009. “2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids”. Beilstein Journal of Organic Chemistry 5 (43).
Nahrwold, M., Stoncius, A., Penner, A., Neumann, B., Stammler, H. - G., and Sewald, N. (2009). 2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids. Beilstein Journal of Organic Chemistry 5.
Nahrwold, M., et al., 2009. 2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids. Beilstein Journal of Organic Chemistry, 5(43).
M. Nahrwold, et al., “2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids”, Beilstein Journal of Organic Chemistry, vol. 5, 2009.
Nahrwold, M., Stoncius, A., Penner, A., Neumann, B., Stammler, H.-G., Sewald, N.: 2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids. Beilstein Journal of Organic Chemistry. 5, (2009).
Nahrwold, Markus, Stoncius, Arvydas, Penner, Anna, Neumann, Beate, Stammler, Hans-Georg, and Sewald, Norbert. “2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids”. Beilstein Journal of Organic Chemistry 5.43 (2009).
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