Conventionally, there has been made attempts for conducting asymmetric hydrogenation of carbon-carbon double bond of α,β-unsaturated aldehyde using hydrogen gas, and there is known methods for conducting asymmetric hydrogenation of neral or geranial for the purpose of obtaining optically active citronellal which is particularly important as a flavor or fragrance (Patent Literatures 1 and 2). Since these methods are methods for hydrogenating carbon-carbon double bond with hydrogen gas using a small amount of a homogeneous catalyst, auxiliaries are not required so that a large amount of waste is not generated.
There has been reported asymmetric hydrogenation of carbon-carbon double bond of α,β-unsaturated ketone using a combination of Pd black, Pd/C or Pd/TiO2 and (−)-dihydroapovincamic acid ethyl ester, proline or cinchonidine (Non-Patent Literatures 1 to 5).
In addition, there has been reported hydrogen transfer type asymmetric hydrogenation reaction of an α,β-unsaturated compound using an organic asymmetric catalyst and Hantzsch ester (Patent Literature 3 and Non-Patent Literature 6).