Geranylacetone → (6S)-6,10-dimethylundecan-2-one

HRID 709376Notes

Reaction equation

HRID 709376 reaction equation
[CH2:1]([CH2:11][C:12](=[O:14])[CH3:13])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].[CH3:15][C@@H:16]([CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:17][CH2:18][CH2:19][C:20](=[O:22])[CH3:21]>>[CH3:4][C@@H:3]([CH2:5][CH2:6][CH2:7][CH:8]([CH3:10])[CH3:9])[CH2:2][CH2:1][CH2:11][C:12](=[O:14])[CH3:13].[CH3:15][C@H:16]([CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:17][CH2:18][CH2:19][C:20](=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 1549778GeranylacetoneHCID 1551303(6S)-6,10-dimethylundecan-2-one

Product 2

HCID 1551303(6S)-6,10-dimethylundecan-2-oneHCID 1715160(6R)-6,10-dimethylundecan-2-one

Procedure

Specifically, it has been found that using the R-isomer of catalyst of formula (I) in the hydrogenation of E-geranyl acetone (=(E)-6,10-dimethylundeca-5,9-dien-2-one) the hydrogenation product (6S)-6,10-dimethylundecan-2-one is formed in more than 98% in respect to all of the possible stereoisomers (i.e. (6S)-6,10-dimethylundecan-2-one and (6R)-6,10-dimethylundecan-2-one) whereas the corresponding R-isomer is obtained only in amount of less than 2%.

Sources & evidence

ORD record
ord-c711f65616254b5b8b3a3fb1c7350f12
Source dataset
uspto-grants-2015_11
Patent number
US09181163B2

Reaction notes

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