Organocatalytic highly enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes.
The first organocatalytic enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes for the direct synthesis of chiral nitroalkylated naphthoquinone derivatives was investigated. Good yields and excellent enantioselectivities (up to >99% ee) could be achieved. This organocatalytic asymmetric Michael addition provides an efficient route toward the synthesis of optically active functionalized naphthoquinones.
Zhou
Wen-Ming
WM
Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, PRC.
Liu
Han
H
Du
Da-Ming
DM
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D018360:Crystallography, X-Ray; D006900:Hydroxylation; D008958:Models, Molecular; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry
D000475:Alkenes; D002930:Cinchona Alkaloids; D009285:Naphthoquinones; D009574:Nitro Compounds; D013890:Thiourea