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2-Phenyl-tetrahydropyrimidine-4(1H)-ones--cyclic benzaldehyde aminals as precursors for functionalised beta-amino acids.

ABSTRACT: 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.

SUBMITTER: Nahrwold M

PROVIDER: S-EPMC2779662 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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2-Phenyl-tetrahydropyrimidine-4(1H)-ones--cyclic benzaldehyde aminals as precursors for functionalised beta-amino acids.

Nahrwold Markus M Stoncius Arvydas A Penner Anna A Neumann Beate B Stammler Hans-Georg HG Sewald Norbert N

Beilstein journal of organic chemistry 20090914

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 ...[more]

PMID: 19936267

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