Catalytic asymmetric Mannich reaction of glycine Schiff bases with α-amido sulfones as precursors of aliphatic imines.
A general and practical Cu(I)-Fesulphos-catalyzed Mannich reaction of glycinate Schiff bases with aliphatic imines generated in situ from α-amido sulfones is described. Imines with linear and branched alkyl chains, including substrates bearing functional groups, can be efficiently applied. The resulting syn-configured orthogonally protected β-alkyl-α,β-diamino acid derivatives are produced with excellent levels of diastereo- (typically syn/anti >90 : <10) and enantioselectivity (generally ≥90% ee).
Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.
Elier
E
Hernando
Ramón
R
Gómez Arrayás
Juan C
JC
Carretero
D002384:Catalysis; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry*; D013450:Sulfones / Q000737:chemistry*
D007097:Imines; D009942:Organometallic Compounds; D012545:Schiff Bases; D013450:Sulfones; D005998:Glycine