| 2-Phenyl-tetrahydropyrimidine-4(1H)-ones--cyclic benzaldehyde aminals as precursors for functionalised beta-amino acids. | |
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MedLine Citation:
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PMID: 19936267 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Markus Nahrwold; Arvydas Stoncius; Anna Penner; Beate Neumann; Hans-Georg Stammler; Norbert Sewald |
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Publication Detail:
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Type: Journal Article Date: 2009-09-14 |
Journal Detail:
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Title: Beilstein journal of organic chemistry Volume: 5 ISSN: 1860-5397 ISO Abbreviation: Beilstein J Org Chem Publication Date: 2009 |
Date Detail:
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Created Date: 2009-11-25 Completed Date: 2010-05-20 Revised Date: 2010-09-28 |
Medline Journal Info:
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Nlm Unique ID: 101250746 Medline TA: Beilstein J Org Chem Country: Germany |
Other Details:
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Languages: eng Pagination: 43 Citation Subset: - |
Affiliation:
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Bielefeld University, Department of Chemistry, Organic and Bioorganic Chemistry, Universitätsstr. 25, 33615 Bielefeld, Germany. |
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