Primary amine/(+)-CSA salt-promoted organocatalytic conjugate addition of nitro esters to enones.
The combination of 9-amino-9-deoxy-epi-cinchonine and (+)-CSA resulted in a novel primary amine-based organocatalyst for effective iminium activation of alpha,beta-unsaturated ketones. Such a catalytic system could catalyze the conjugate addition of nitroacetate to enones in a highly enantioselective manner, affording the desired adducts in high yields and with up to 99% ee.
Liu
Chen
C
Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Republic of Singapore, 117543.
Lu
Yixin
Y
D000085:Acetates / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002164:Camphor / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D012492:Salts / Q000737:chemistry; D013237:Stereoisomerism
D000085:Acetates; D000588:Amines; D007659:Ketones; D012492:Salts; C028257:nitroacetic acid; D002164:Camphor; C006881:10-camphorsulfonic acid