Document Detail


2-Phenyl-tetrahydropyrimidine-4(1H)-ones--cyclic benzaldehyde aminals as precursors for functionalised beta-amino acids.
MedLine Citation:
PMID:  19936267     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Markus Nahrwold; Arvydas Stoncius; Anna Penner; Beate Neumann; Hans-Georg Stammler; Norbert Sewald
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Publication Detail:
Type:  Journal Article     Date:  2009-09-14
Journal Detail:
Title:  Beilstein journal of organic chemistry     Volume:  5     ISSN:  1860-5397     ISO Abbreviation:  Beilstein J Org Chem     Publication Date:  2009  
Date Detail:
Created Date:  2009-11-25     Completed Date:  2010-05-20     Revised Date:  2013-05-23    
Medline Journal Info:
Nlm Unique ID:  101250746     Medline TA:  Beilstein J Org Chem     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  43     Citation Subset:  -    
Affiliation:
Bielefeld University, Department of Chemistry, Organic and Bioorganic Chemistry, Universitätsstr. 25, 33615 Bielefeld, Germany.
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