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.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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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
ISSN
1860-5397
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.
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. doi:10.3762/bjoc.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.
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 (2009).
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