Organic small molecule catalyst of aqueous phase asymmetric direct aldol condensation reaction, and preparing method and use thereof

Abstract

The invention discloses an organic molecular catalyst of water-phase asymmetrical hydroxy-aldehyde condensing reaction, which is characterized by the following: possessing central chirality and axial chirality to catalyze asymmetrical hydroxy-aldehyde condensing reaction in the water phase; improving receiving rate; obtaining the product with diastereomer selectivity and high-optical purity.

Description

technical field [0001] The invention belongs to the field of asymmetric catalysis of organic chemistry, in particular to an organic small molecule chiral catalyst used for direct aldol condensation reaction in water phase. Background technique [0002] The aldol condensation reaction is one of the most important reactions in organic chemistry for the formation of C-C bonds. Highly functionalized products can be obtained through aldol condensation reactions and generate new chiral centers. In the synthesis of complex molecules and the preparation of optically active small molecule building blocks, many examples of asymmetric aldol condensations can be found (Comprehensive Organic Synthesis; Pergamon Press: NewYork, 1991: J.Am.Chem.Soc.1981, 103, 2127: J. Am. Chem. Soc. 1989, 111, 5493: J. Am. Chem. Soc. 1997, 119, 2586). In the reaction of asymmetric aldol condensation, the catalyzed direct asymmetric aldol condensation reaction has become a research hotspot in recent years...

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Problems solved by technology

However, these two catalysts are only suitable for the reaction between acetone and aldehyde, and the results are not satisfactory when cyclohexanone is used as the substrate.

Xiao Wenjing and others reported that another class of proline amide derivatives can well catalyze the asymmetric direct aldol condensation reaction between cyclohexanone and aldehyde, but the solvent they use is chloroform, which is not environmentally friendly. process, and high selectivity can only be obtained at low temperature (Org.Lett.2005, 7, 4543)

For the needs of green chemistry, some organic small molecule catalysts have been designed and found to catalyze the reaction between cyclohexanone and aldehyde in aqueous phase, but these catalysts cannot simultaneously obtain high yield, diastereoselectivity and Optical selectivity (Angew.Chem.Int.Ed.2006, 45, 958: J.Am.Chem.Soc.2006, 128, 734: Chem.Commun.2006, 2801)

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