Enantioselective synthesis of both enantiomers of methyl dihydrojasmonate using solid-liquid asymmetric phase-transfer catalysis.
Both enantiomers of methyl dihydrojasmonate (-)-1 and (+)-1 were obtained by a short route using asymmetric Michael addition of dimethyl malonate onto pentyl enone 3, followed by nonracemizing demethoxycarbonylation. The key enantioselective step involves a new system of asymmetric solid-liquid phase-transfer catalysis using solvent-free conditions. Enantiomeric excess as high as 90% (91% yield) was achieved.
Perrard
T
T
Laboratoire des Fonctions Azotées et Oxygénées Complexes - IRCOF, UPRES-A CNRS 6014, Faculté des Sciences, rue Tesnière, F-76821 Mont Saint Aignan Cedex, France.
Plaquevent
J C
JC
Desmurs
J R
JR
Hébrault
D
D
D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis*; D010476:Perfume / Q000138:chemical synthesis; D010936:Plant Extracts / Q000737:chemistry; D010944:Plants / Q000737:chemistry; D013237:Stereoisomerism
D003517:Cyclopentanes; D010476:Perfume; D010936:Plant Extracts