Stereoselective synthesis of highly functionalized nitrocyclopropanes through the organocatalyic Michael-addition-initiated cyclization of bromonitromethane and β,γ-unsaturated α-ketoesters.
A highly diastereo- and enantioselective cyclopropanation of β,γ-unsaturated α-ketoesters with bromonitromethane has been successfully developed through a domino Michael-addition/intramolecular-alkylation strategy. Acceptable yields (up to 89%) and enantioselectivities (up to 96% ee) have been obtained.
Institute and State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071 (P. R. China), Fax: (+86) 022-23503627.
Haijian
H
Yu
Qiaohui
Q
Wang
Youming
Y
Wang
Haibing
H
Song
Zhenghong
Z
Zhou
Chuchi
C
Tang
D000478:Alkylation; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry*; D004952:Esters; D004980:Ethane / Q000031:analogs & derivatives* / Q000737:chemistry; D008968:Molecular Conformation; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D003521:Cyclopropanes; D004952:Esters; D009574:Nitro Compounds; C533588:bromonitromethane; D004980:Ethane
Michael addition; alkylation; asymmetric catalysis; nitrocyclopropanes; organocatalysis