An efficient synthesis of chiral diamines with rigid backbones: application in enantioselective Michael addition of malonates to nitroalkenes.
A new and efficient route for synthesis of enantiomerically pure biisoindoline and its isomer based on the diaza-Cope rearrangement reaction with chiral 1,2-bis(2-hydroxylphenyl)-1,2-diaminoethane as starting material has been developed. The newly prepared biisoindoline was employed as a chiral ligand in the Ni(II)-catalyzed enantioselective Michael addition of malonates to conjugated nitroalkenes, and good to excellent enantioselectivities were obtained.
Zhu
Qiming
Q
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. China.
Huang
Hanmin
H
Shi
Dengjian
D
Shen
Zhiqiang
Z
Xia
Chungu
C
D000475:Alkenes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000475:Alkenes; D003959:Diamines; D008314:Malonates