We have stereo selectively synthesised P-hydroxy-a-amino acids beta-substituted with non-aromatic heterocycles by means of a condensation reaction between enantiomerically pure heterocyclic aldehydes and the (R)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (Schollkopf's reagent) as a chiral auxiliary. The stereocontrolled addition gave mixtures of diastereoisomers whose steric configurations were assigned on the basis of spectroscopic data and X-ray analysis. Upon controlled hydrolysis, the adducts were transformed into the corresponding methyl esters of beta-hydroxy-beta-heterocyclic substituted a-amino acids.

Stereoselective synthesis of beta-hydroxy-alpha-amino acids beta-substituted with non-aromatic heterocycles / G. Cremonesi, P. Dalla Croce, F. Fontana, A. Forni, C. La Rosa. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 18:4(2007), pp. 1667-1675. [10.1016/j.tetasy.2007.05.040]

Stereoselective synthesis of beta-hydroxy-alpha-amino acids beta-substituted with non-aromatic heterocycles

G. Cremonesi
Primo
;
P. Dalla Croce
Secondo
;
F. Fontana;C. La Rosa
Ultimo
2007

Abstract

We have stereo selectively synthesised P-hydroxy-a-amino acids beta-substituted with non-aromatic heterocycles by means of a condensation reaction between enantiomerically pure heterocyclic aldehydes and the (R)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (Schollkopf's reagent) as a chiral auxiliary. The stereocontrolled addition gave mixtures of diastereoisomers whose steric configurations were assigned on the basis of spectroscopic data and X-ray analysis. Upon controlled hydrolysis, the adducts were transformed into the corresponding methyl esters of beta-hydroxy-beta-heterocyclic substituted a-amino acids.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/36365
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