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Catalytic Enantioselective Addition of Propionate Units to Imines: An Efficient Synthesis of anti ‐ α ‐Methyl‐ β ‐Amino Acid Derivatives
Author(s) -
Kobayashi Shū,
Kobayashi Jun,
Ishiani Haruro,
Ueno Masaharu
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020916)8:18<4185::aid-chem4185>3.0.co;2-6
Subject(s) - enantioselective synthesis , chemistry , catalysis , selectivity , enantiomer , enantiomeric excess , propionate , substrate (aquarium) , reactivity (psychology) , combinatorial chemistry , chiral ligand , organic chemistry , ligand (biochemistry) , medicine , biochemistry , oceanography , alternative medicine , receptor , pathology , geology
Optically active anti ‐ α ‐methyl‐ β ‐amino acid derivatives have been prepared based on catalytic enantioselective addition of propionate units to simple and inert imines using a chiral zirconium complex. High reactivity and selectivity with wide substrate scope were attained by using a new chiral ligand, ( R )‐6,6′‐bis(pentafluoroethyl)‐1,1′‐bi‐2‐naphthol (( R )‐6,6′‐C 2 F 5 BINOL). The reactions using geometrically isomeric ketene silyl acetals gave excellent anti ‐selectivity with high enantiomeric excess in both cases. Synthetic utility of this reaction has been demonstrated by the preparation of various anti ‐ α ‐methyl‐ β ‐amino acid and trans ‐3,4‐disubstituted β ‐lactam derivatives.