Catalytic asymmetric synthesis of a nitrogen analogue of dialkyl tartrate by direct mannich reaction under phase-transfer conditions.
[reaction: see text] Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with alpha-imino ester 4 has been accomplished with high enantioselectivity by the utilization of N-spiro C(2)-symmetric chiral quaternary ammonium bromide 2 as a catalyst. This methodology enables the catalytic asymmetric synthesis of differentially protected 3-aminoaspartate, a nitrogen analogue of dialkyl tartrate. The product (syn-5) was converted into a precursor (6) of streptolidine lactam.
Ooi
Takashi
T
Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.
Kameda
Minoru
M
Fujii
Jun-Ichi
J
Maruoka
Keiji
K
D000473:Alkanes / Q000138:chemical synthesis*; D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism; D013644:Tartrates / Q000138:chemical synthesis*
D000473:Alkanes; D007202:Indicators and Reagents; D013644:Tartrates; D009584:Nitrogen; D005998:Glycine