Trans-stereoselectivity in the reaction between homophthalic anhydride and imines.
The reaction between homophthalic anhydride and imines in the presence of TiCl4 and diisopropyl ethyl amine is trans-selective. Under these conditions, the reaction using homochiral imines can be highly diastereoselective, thus allowing the synthesis of enantiopure 1,2,3,4-tetrahydro-1-oxoquinoline-4-carboxylic acids.
Vara
Yosu
Y
IkerChem Ltd., Tolosa Etorbidea 72, 20018 San Sebastián-Donostia, Spain.
Bello
Tamara
T
Aldaba
Eneko
E
Arrieta
Ana
A
Pizarro
José L
JL
Arriortua
María I
MI
Lopez
Xabier
X
Cossío
Fernando P
FP
D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010796:Phthalic Anhydrides / Q000737:chemistry*; D013237:Stereoisomerism
D007097:Imines; D010796:Phthalic Anhydrides