HIGHLY DIASTEREOSELECTIVE AZA-ALDOL REACTIONS OF A CHIRAL NI(II) COMPLEX OF GLYCINE WITH IMINES - AN EFFICIENT ASYMMETRIC APPROACH TO 3-PERFLUOROALKYL-2,3-DIAMINO ACIDS

Authors
SOLOSHONOK VA AVILOV DV KUKHAR VP VANMEERVELT L MISCHENKO N
Citation
Va. Soloshonok et al., HIGHLY DIASTEREOSELECTIVE AZA-ALDOL REACTIONS OF A CHIRAL NI(II) COMPLEX OF GLYCINE WITH IMINES - AN EFFICIENT ASYMMETRIC APPROACH TO 3-PERFLUOROALKYL-2,3-DIAMINO ACIDS, Tetrahedron letters, 38(26), 1997, pp. 4671-4674
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
26
Year of publication
1997
Pages
4671 - 4674
Database
ISI
SICI code
0040-4039(1997)38:26<4671:HDAROA>2.0.ZU;2-Q
Abstract
The LiCl/base-assisted asymmetric aldol-type addition reaction between the N-(p-methoxyphenyl)imine of trifluoroacetaldehyde and the chiral non-racemic NI(II) complex of the Schiff base of glycine with (S)-o-[N -(N-benzylprolyl)amino]benzophenone was found to proceed with excellen t chemical and stereochemical outcomes allowing for an efficient acces s to hitherto unknown stereochemically defined beta-perfluoroalkyl-alp ha,beta-diamino carboxylic acids. A mechanistic rationale for the obse rved stereochemical preferences is proposed. (C) 1997 Elsevier Science Ltd.