Enantioselective synthesis of both enantiomers of dimethyl cis-(4-acetoxycyclopent-2-enyl)malonate, key intermediates for epijasmonate.
Both enantiomers (3 and 4) of dimethyl cis-(4-acetoxycyclopent-2-enyl)malonate (3), known intermediates for the synthesis of epijasmonate, were prepared in an enantio-enriched form from common starting material 2 based on desymmetrization of the meso-character by palladium-catalyzed asymmetric allylic alkylation.
Tanimori
Shinji
S
Department of Applied Biological Chemistry, Graduate School of Agriculture and Life Sciences, Osaka Prefecture University, Sakai, Japan. tanimori@biochem.osakafu-u.ac.jp
Tsuji
Yuko
Y
Kirihata
Mitsunori
M
D000478:Alkylation; D002384:Catalysis; D003517:Cyclopentanes / Q000737:chemistry*; D007202:Indicators and Reagents; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008314:Malonates / Q000737:chemistry*; D010165:Palladium; D010937:Plant Growth Regulators / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D003517:Cyclopentanes; D007202:Indicators and Reagents; D008024:Ligands; D008314:Malonates; D010937:Plant Growth Regulators; C468153:dimethyl-(4-acetoxycyclopent-2-enyl)malonate; C468154:epijasmonate; D010165:Palladium