Farnesyl acetone → (6R,10R)-6,10,14-trimethylpentadecan-2-one

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Reaction Steps

Specifically, it has been found that using the R-isomer of catalyst of formula (I) in the hydrogenation of E,E-farnesylacetone (=(5E,9E)-6,10,14-trimethylpentadeca-5,9,13-trien-2-one) the hydrogenation product (6S,10S)-6,10,14-trimethylpentadecan-2-one is formed in more than 96% in respect to all of the possible stereoisomers (i.e. (6S,10S)-6,10,14-trimethylpentadecan-2-one, (6S,10R)-6,10,14-trimethylpentadecan-2-one, (6R,10S)-6,10,14-trimethylpentadecan-2-one and (6R,10R)-6,10,14-trimethylpentadecan-2-one). Hence, the corresponding (6S,10R)- and (6R,10S)- and (6R,10R)-isomers are only formed only in smaller amounts.

Provenance & Evidence