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| - Model Studies toward the Synthesis of Dihydropyrimidinyl andPyridyl α-Amino Acids via Three-Component Biginelli andHantzsch Cyclocondensations
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| - A novel and versatile strategy for the synthesis of heterocyclic α-amino acids has been described.The use of components (aldehyde or β-ketoester) bearing a masked glycinyl moiety in Biginelli andHantzsch cyclocondensations allowed access to the 4-dihydropyrimidinyl-α-glycines, 4-dihydropyrimidinyl-α-alanines, 4-pyridyl-α-alanines, and 2-pyridyl-α-alanines classes. Dihydropyrimidinyl-amino acids were obtained as a mixture of diastereoisomers due to the formation of the stereocenterat C4 of the dihydropyrimidinone ring. Individual stereoisomers were isolated as pure compoundsand their structures were assigned with the aid of X-ray crystallography and chiroptical properties.The enantiomeric purity of a representative selection of the above amino acids was greater than96% as verified by derivatization to the corresponding Mosher's amides and subsequent 1H and19F NMR spectroscopy. Incorporation of the 4-pyridyl-α-alanine derivative into a peptide chain isalso described.
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