Tetrahedron

A stereocontrolled synthesis of a new class of 3, 4, 5, 6-tetrahydropyrimidine-based chiral amino acids

A Zamri, F Sirockin, MA Abdallah

Index: Zamri, Adel; Sirockin, Finton; Abdallah, Mohamed A. Tetrahedron, 1999 , vol. 55, # 16 p. 5157 - 5170

Full Text: HTML

Citation Number: 15

Abstract

The stereocontrolled synthesis of seven 2-substituted-4-carboxy-3, 4, 5, 6- tetrahydropyrimidines bearing either one chiral center at C-4 or two chiral centers at C-4 and C-8 was performed by condensation of (S)-or (R)-2, 4-diaminobutyric acid (Daba) with iminoethers derived from glycine,(S)-and (R serine,(S)-and (R)-tyrosine. Under the conditions reported, epimerization was always completely prevented at the C-4 center, ...