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
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1.4 CHEMICAL SCIENCES, Organic Chemistry
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 a or b positions of the aziridine. However, the regiochemical outcome is not predictable.
Kelleher, F. and O'Brien, K. 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. Tetrahedron Letters, October 2013.