1-Cyclopentene-1-acetic acid, 3-oxo-2-pentyl-, methyl ester → Hedione

Participants

Reaction Steps

In a glovebox, into a 10 ml glass vial were placed 15.0 mg (0.0250 mmole) of [((R,R)-Me-Duphos)Ru(H)(cyclooctatriene)]BF4, 5.62 ml of CH2Cl2 and 11.23 g (50.0 mmole) of methyl 3-oxo-2-pentyl-1-cyclopentene-1-acetate. The resulting yellow solution was placed in a 75 ml autoclave, purged with hydrogen and pressurized to 90 bar of hydrogen. After 6 hours, the solution was exposed to air and passed through a column of silica gel to separate the catalyst. This gave a 99% yield of the desired Hedione® product with the following ratios of isomers: cis/trans=98/2; (+)-cis/(−)-cis=82.3/17.7, 64.6% ee.

Provenance & Evidence