Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and Their Derivatization Utilizing the Sonogashira Coupling Reaction in the Enantioselective Synthesis of α-Substituted β-Amino Acids

A convenient, one-pot procedure for the synthesis of 1-benzoyl-2(S)-substituted-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones by tandem decarboxylation/β-iodination of the corresponding 6-carboxy-perhydropyrimidin-4-ones was developed. In addition, several 1-benzoyl-2(S)-substituted-5-bromo-2,3-dihydro-4...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2007-06, Vol.72 (13), p.4822-4825
Main Authors: Díaz-Sánchez, Blanca R, Iglesias-Arteaga, Martín A, Melgar-Fernández, Roberto, Juaristi, Eusebio
Format: Article
Language:English
Subjects:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Catalysis
Halogens - chemistry
Hydrogen - chemistry
Hydrolysis
Molecular Structure
Pyridines - chemistry
Pyrimidinones - chemical synthesis
Pyrimidinones - chemistry
Stereoisomerism
Uracil - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A convenient, one-pot procedure for the synthesis of 1-benzoyl-2(S)-substituted-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones by tandem decarboxylation/β-iodination of the corresponding 6-carboxy-perhydropyrimidin-4-ones was developed. In addition, several 1-benzoyl-2(S)-substituted-5-bromo-2,3-dihydro-4(H)-pyrimidin-4-ones were readily prepared by bromination of 1-benzoyl-2(S)-substituted-2,3-dihydro-4(H)-pyrimidin-4-ones. Subsequently, Sonogashira coupling of the halogenated heterocyclic enones with various terminal alkynes produced 1-benzoyl-2(S)-isopropyl-5-alkynyl-2,3-dihydro-4(H)-pyrimidin-4-ones in good yields. Hydrogenation of the unsaturated C−C moieties in the Sonogashira products followed by acid hydrolysis afforded highly enantioenriched α-substituted β-amino acids.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0705115