Stereoselective synthesis of β-hydroxy-α-amino acids β-substituted with non-aromatic heterocycles |
| |
Institution: | 1. Istituto di Chimica Organica ‘A. Marchesini’, Facoltà di Farmacia, V. Venezian 21, I-20133 Milano, Italy;2. Dipartimento di Chimica Organica e Industriale and C.N.R.-I.S.T.M., V. Venezian 21, I-20133 Milano, Italy;3. C.N.R.-I.S.T.M., V. Golgi,19, I-20133 Milano, Italy |
| |
Abstract: | We have stereoselectively synthesised β-hydroxy-α-amino acids β-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 (Schöllkopf’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 β-hydroxy-β-heterocyclic substituted α-amino acids. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|