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Synthesis of orthogonally protected 1,2-diaminopropanoic acids by ring-opening of 3-unsubstituted N-activated aziridine 2-carboxylates with para-methoxybenzylamine: a study of the regioselectivity of the reaction
Authors:Keith O&rsquo  Brien,Fintan Kelleher
Affiliation:Molecular Design and Synthesis Group, Centre of Applied Science for Health, Institute of Technology Tallaght, Dublin 24, Ireland
Abstract:
Orthogonally protected 1,2-diaminopropanoic acids (DAPs) have been synthesised in good yields by the ring-opening of 3-unsubstituted N-activated aziridine 2-carboxylates with para-methoxybenzylamine. The choice of both the N-activating group and ester alkyl group had a significant influence on the ratio of attack at the α or β positions of the aziridine. However, the regiochemical outcome is not predictable.
Keywords:1,2-Diaminopropanoic acids (DAPs)   Aziridine 2-carboxylates   Ring-opening   Regioselectivity
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