Asymmetric synthesis of silylated alpha-amino acid esters through dynamic kinetic resolution.
Esters of three types of silylated alpha-amino acids have been prepared from appropriate zirconaaziridines. Slow addition (syringe pump) of the (R,R) carbonate of trans-stilbene gave metallacycles with the maximum possible diastereomeric excess (as determined by the diastereomeric excess produced by the Hoffmann test-the same reaction but with racemic carbonate). Methanolysis gave esters (RO(2)C)CH(R')(NHPh) (R' = Me(3)Si, Me(3)SiCH(2), and p-Me(3)SiC(6)H(4)) with the same optical purity at the alpha carbon.
Chen
Jian-Xin
JX
Department of Chemistry, Columbia University, New York, New York 10027, USA.
Tunge
Jon A
JA
Norton
Jack R
JR
D000465:Algorithms; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D002851:Chromatography, High Pressure Liquid; D004952:Esters / Q000737:chemistry*; D005663:Furans / Q000737:chemistry; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry
D000596:Amino Acids; D004952:Esters; D005663:Furans; D009942:Organometallic Compounds; D015040:Zirconium; D012825:Silicon