Highly enantioselective synthesis of nitrocyclopropanes via organocatalytic conjugate addition of bromomalonate to alpha,beta-unsaturated nitroalkenes.
Highly enantioselective synthesis of nitrocyclopropanes was achieved via the organocatalytic conjugate addition of dimethyl bromomalonate to nitroalkenes and the consequent intramolecular cyclopropanation. 6'-Demethyl quinine was found to be the efficient catalyst. Excellent enantioselectivities, diastereoselectivities, and good yields were obtained for a variety of aryl or heteroaryl nitroethylenes.
Xuan
Yi-Ning
YN
Industrial Institute of Fine Chemicals and Synthetic Drugs, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.
Nie
Shao-Zhen
SZ
Dong
Li-Ting
LT
Zhang
Jun-Min
JM
Yan
Ming
M
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011803:Quinine / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D003521:Cyclopropanes; D008314:Malonates; D009574:Nitro Compounds; C517405:bromomalonic acid; D011803:Quinine