Diethyl Ether → Methyl dihydrojasmonate, cis-(+)-

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The reaction was carried out analogously to that described in example 6, but using 100 g (446 mmole) of methyl 3-oxo-2-pentyl-1-cyclopentene-acetate, 427 mg (1.34 mmole) of [(COD)Ru(2-methylallyl)2 ], 410 mg (1.34 mmole) of (-)-Me-DuPHOS and 26.5 ml of HBF4.O(C2H5)2 in dichloromethane (0.1M, 2.68 mmole). This corresponds to a catalyst concentration of 0.3 mole %, relative to the substrate. 170 ml of dichloromethane were added, and the mixture was hydrogenated at a temperature of 7.5° C. and a pressure of 5×106Pa for 70 h to obtain methyl (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate in 99% yield, cis/trans ratio=99.2/0.8 and (+)-cis/(-)-cis ratio=84/16.

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