A method for constructing an axially chiral cycloalkyl amine compound in one pot
A one-pot synthesis method for axially chiral cycloalkylamine compounds was developed using a chiral phosphoric acid catalyst and Hans ester reducing agent. This method solved the asymmetric synthesis problem of axially chiral alkylene cycloalkanes and spiroalkanes, achieving efficient, simple, and environmentally friendly construction of axially chiral frameworks.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- SHANGHAI TECH UNIV
- Filing Date
- 2026-04-22
- Publication Date
- 2026-07-17
AI Technical Summary
Existing technologies have limited asymmetric synthesis methods for axially chiral alkylene cycloalkanes and axially chiral spiranes, making it difficult to efficiently construct axially chiral skeletons containing amino functional groups. Furthermore, existing methods suffer from narrow applicability, complex operation, and environmental unfriendliness.
A one-pot synthesis method was adopted, using a chiral phosphoric acid catalyst and hans ester as a reducing agent to react an aromatic amine compound with a prochiral ketone compound in an anhydrous organic solvent to generate axially chiral cycloalkylamine compounds, including the asymmetric reductive amination reaction of 7-arylspiro[3.5]nonane-2-one and 4-(arylmethylene)cyclohexanone.
This method enables the efficient construction of axially chiral spiroalkane and alkylene cycloalkane skeletons, exhibiting excellent enantioselectivity and broad substrate applicability. It is simple to operate, low in cost, and environmentally friendly, avoiding the shortcomings of chiral HPLC separation and complex biocatalysts.
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