Enantioselective Synthesis of Both Enantiomers of Methyl Dihydrojasmonate Using Solid−Liquid Asymmetric Phase-Transfer Catalysis

Citations Over TimeTop 12% of 2000 papers

Abstract

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.

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