Enantioselective synthesis of imidazolines with quaternary stereocenters by organocatalytic reaction of N-(heteroarenesulfonyl)imines with isocyanoacetates.
An organocatalytic enantioselective Mannich-type reaction of isocyanoacetate with N-sulfonylimines catalyzed by chiral thioureas derived from quinine yielded 2-imidazolines with high diastereo- and enantioselectivities (up to >99:1 dr. and 96% ee). This reaction provided a convenient route to access various imidazolines and related α,β-diamino acids having a quaternary carbon center in high enantiomeric purities.
Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Nagoya 466-8555, Japan. snakamur@nitech.ac.jp
Shuichi
S
Nakamura
Yuri
Y
Maeno
Mutsuyo
M
Ohara
Akiko
A
Yamamura
Yasuhiro
Y
Funahashi
Norio
N
Shibata
D019342:Acetic Acid / Q000737:chemistry*; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D048288:Imidazolines / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
D003486:Cyanides; D048288:Imidazolines; D007097:Imines; D013449:Sulfonamides; D019342:Acetic Acid