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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, Fintan Kelleher, Keith O'Brien
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, Fintan Kelleher, Keith O'Brien
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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.