Silicon-substituted chiral amine as well as preparation method and application thereof

• Main Authors: WU QINGDIAN, SANG HAORUI, ZHANG XINYU, ZHU SHOUFEI, ZHANG YANDONG, LIU XIAOTAO
• Format: Patent
• Language: Chinese; English
• Published: 25.04.2023
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY; CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY; PERFORMING OPERATIONS; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL; THEIR RELEVANT APPARATUS; TRANSPORTING

The invention discloses a silicon-substituted chiral amine and a preparation method and application thereof.D-proline serves as a raw material, a gem-diaryl substituted chiral tetrahydropyrrole catalyst is obtained through substitution, addition, reduction and other reactions, the catalyst is applied to an asymmetric hydrogenation reaction of citral, and the specific process includes the steps that a solvent is not used or in a solvent, and the chiral tetrahydropyrrole is subjected to a one-step reaction to obtain the silicon-substituted chiral amine. The (R)-citronellal is prepared by carrying out asymmetric hydrogenation reaction on citral in a hydrogen atmosphere under the action of an additive under combined catalysis of a silicon-substituted chiral amine catalyst and a palladium catalyst. The asymmetric hydrogenation reaction has the following characteristics: under the reaction condition of 1 mol% of chiral amine catalyst, the (R)-citronellal can be obtained at the optimal ee value of 85%. The character