Design, synthesis, and application of tartaric acid derived N-spiro quaternary ammonium salts as chiral phase-transfer catalysts.
A novel class of tartaric acid-derived N-spiro quaternary ammonium salts was synthesised starting from known TADDOLs. These compounds were found to catalyse the asymmetric α-alkylation of glycine Schiff bases with high enantioselectivities and in good yields.
Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstraße 69, 4040 Linz, Austria. Mario.waser@jku.at
Mario
M
Waser
Katharina
K
Gratzer
Richard
R
Herchl
Norbert
N
Müller
D002384:Catalysis; D005998:Glycine / Q000737:chemistry; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D012492:Salts / Q000138:chemical synthesis / Q000737:chemistry; D012545:Schiff Bases / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013644:Tartrates / Q000138:chemical synthesis* / Q000737:chemistry*
D000644:Quaternary Ammonium Compounds; D012492:Salts; D012545:Schiff Bases; D013141:Spiro Compounds; D013644:Tartrates; D005998:Glycine; C029768:tartaric acid