Scandium Triflate Catalyzed Aminolysis of meso-Aziridines

Abstract

The aminolysis of meso-N-phenyl aziridines is efficiently catalyzed with just 1 mol% of Sc(OTf)₃ and furnishes valuable 1,2-diamines in good to excellent yields.

amine - aziridine - catalysis - 1,2-diamine - scandium

References and Notes

Reviews:

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Reviews:

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8 Scandium triflate has been shown to catalyze the addition of acid anhydrides to aziridines, see: Yadav JS. Reddy BVS. Sadashiv K. Harikishan K. Narsaiah AV. J. Mol. Catal. A: Chem.  2004,  220:  153 

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10

General Procedure for Ring Opening of meso -Aziridines
To a solution of Sc(OTf)₃ (5 mg, 0.01 mmol) in CH₂Cl₂ (5 mL), were added N-phenyl aziridine (1.00 mmol) and amine (1.50 mmol), and the mixture was stirred at r.t. for 1 h (monitored by TLC). The solvent was removed in vacuo and the crude product was purified through flash chromatog-raphy using pentane-EtOAc (15:1) as eluent. For analytical and spectroscopic details of the products see ref. 3.