Document Type
Article
Rights
This item is available under a Creative Commons License for non-commercial use only
Disciplines
Organic Chemistry
Abstract
Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para-methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding b-methyl azalanthionines have, so far, been unsuccessful.
Recommended Citation
O'Brien, Keith; Ó Proinsias, Keith; and Kelleher, Fintan, "Studies on the Synthesis of Orthogonally Protected Azalanthionines, and of Routes towards b-Methyl Azalanthionines, by Ring-Opening of N-Activated Aziridine-2-Crboxylates" (2014). Articles. 32.
https://arrow.dit.ie/ittsciart/32
Publication Details
Tetrahedron (2014), doi: 10.1016/j.tet.2014.06.011