Highly enantioselective organocatalytic Michael addition of nitroalkanes to 4-oxo-enoates.
A useful Michael addition reaction using nitroalkanes as the nucleophile and 4-oxo-enoates as the Michael acceptor has been disclosed, and the reaction allows expedient access to functionalized chiral gamma-keto esters in high yields and excellent enantioselectivities (up to 98% ee), with a low catalyst loading.
Lu
Hai-Hua
HH
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China.
Wang
Xu-Fan
XF
Yao
Chang-Jiang
CJ
Zhang
Jian-Ming
JM
Wu
Hong
H
Xiao
Wen-Jing
WJ
D000473:Alkanes / Q000737:chemistry*; D002087:Butyrates / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D009574:Nitro Compounds / Q000737:chemistry*; D009930:Organic Chemicals / Q000737:chemistry*; D013237:Stereoisomerism
C508635:6-(nitrooxy)hexyl-(2z)-4-(acetyloxy)-3-(4-(methylsulfonyl)phenyl)-2-phenylbut-2-enoate; D000473:Alkanes; D002087:Butyrates; D009574:Nitro Compounds; D009930:Organic Chemicals