Efficient Synthesis of α,β-Diamino Acid Derivatives by In(III)-Catalyzed Regioselective Addition of Amines to Aziridines

Abstract

An efficient catalytic method for the synthesis of α, β-diamino acid derivatives has been developed via regioselective ring opening of aziridines by amines in the presence of indium(III) salt under very mild reaction conditions.

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GRAPHICAL ABSTRACT

Keywords:

• Amines
• aziridines
• catalytic synthesis
• α,β-diamino acid
• indium(III) salt

ACKNOWLEDGMENT

We are grateful for the financial support from the National Science Foundation of China (20802072).

Notes

^a Reaction conditions: compound 1 (0.4 mmol) and PMPNH₂ (0.6 mmol) in DCM (1 mL), time (24 h).

^b Isolated yields based on substrate 1.

^c The ratio of 2a:3a refers to isolated yields.

^a Reaction conditions: In(OTf)₃ (10 mol %), compound 1 (0.4 mmol), PMPNH₂ (0.6 mmol), solvent (1 mL), time (24 h).

^b Isolated yields based on substrate 1.

^c The ratio of 2a:3a refers to isolated yields.

^a Reaction conditions: compound 1 (0.4 mmol), amine (0.6 mmol), In(OTf)₃ (10 mol %), DCM (1 mL).

^b Isolated yields based on substrate 1.

^c The ratio of 2:3 refers to isolated yields.