SYNTHESIS OF BOTH ENANTIOMERS OF BETA,BETA-DIPHENYL-ALPHA-ALANINE (DIP) FROM GLYCINE USING (S)-2-[(N-BENZYLPROLYL)AMINO]BENZOPHENONE OR (R)-2-[(N-BENZYLPROLYL)AMINO]BENZOPHENONE AS A REUSABLE CHIRAL AUXILIARY

Authors
TARAROV VI SAVELEVA TF KUZNETSOV NY IKONNIKOV NS ORLOVA SA BELOKON YN NORTH M
Citation
Vi. Tararov et al., SYNTHESIS OF BOTH ENANTIOMERS OF BETA,BETA-DIPHENYL-ALPHA-ALANINE (DIP) FROM GLYCINE USING (S)-2-[(N-BENZYLPROLYL)AMINO]BENZOPHENONE OR (R)-2-[(N-BENZYLPROLYL)AMINO]BENZOPHENONE AS A REUSABLE CHIRAL AUXILIARY, Tetrahedron : asymmetry, 8(1), 1997, pp. 79-83
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
1
Year of publication
1997
Pages
79 - 83
Database
ISI
SICI code
0957-4166(1997)8:1<79:SOBEOB>2.0.ZU;2-G
Abstract
Preparative syntheses of enantiopure (S)- and (R)-Dip by alpha-C-alkyl ation with Ph(2)CHX (X=Cl or Br) of the glycine moiety in a Ni(II) Sch iff's base complex 1 derived from glycine and (S)- or (R)-[(N-benzylpr olyl)amino]benzophenone (BPB) is described. The diastereoselectivity o f the alkylation with PhCH(2)Br in DMF in the presence of NaOH is both kinetically and thermodynamically controlled. (C) 1997, Elsevier Scie nce Ltd. All rights reserved.