Catalytic enantioselective silylation of N-sulfonylimines: asymmetric synthesis of α-amino acids from CO2 via stereospecific carboxylation of α-amino silanes.
A catalytic enantioselective silylation of N-tert-butylsulfonylimines using a Cu-secondary diamine complex was demonstrated. The resulting optically active α-amino silanes could be carboxylated under a CO2 atmosphere (1 atm) to afford the corresponding α-amino acids in a stereoretentive manner. This two-step sequence provides a new synthetic protocol for optically active α-amino acids from gaseous CO2 and imines in the presence of a catalytic amount of a chiral source.
Faculty of Pharmaceutical Sciences, Hokkaido University , Sapporo 060-0812, Japan.
Tsuyoshi
T
Mita
Masumi
M
Sugawara
Keisuke
K
Saito
Yoshihiro
Y
Sato
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D003959:Diamines / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
D000596:Amino Acids; D002264:Carboxylic Acids; D003959:Diamines; D007097:Imines; C482356:N-sulfonylimine; D012821:Silanes; D013450:Sulfones