Studies on the Synthesis of Orthogonally Protected Azalanthionines, and of Routes towards b-Methyl Azalanthionines, by Ring-Opening of N-Activated Aziridine-2-Crboxylates

Authors

Keith O'Brien, Technological University DublinFollow
Keith Ó Proinsias, Technological University Dublin
Fintan Kelleher, Technological University DublinFollow

Document Type

Article

Rights

Available under a Creative Commons Attribution Non-Commercial Share Alike 4.0 International Licence

Disciplines

Organic Chemistry

Publication Details

Tetrahedron (2014), doi: 10.1016/j.tet.2014.06.011

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.tudublin.ie/ittsciart/32

Funder

Higher Education Authority