Use of the Mitsunobu Reaction in the Synthesis of Orthogonally Protected a,b-Diaminopropionic Acids

Authors

Fintan Kelleher, Technological University DublinFollow
Keith Ó Proinsias, Technological University Dublin

Document Type

Article

Rights

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

Disciplines

Organic Chemistry

Publication Details

Tetrahedron Letters, 48(28):4879-4882. DOI:10.1016/j.tetlet.2007.05.064

Abstract

Orthogonally protected a,b-diaminopropionic acids have been synthesised in good yields by the reaction of N-trityl L-serine esters with N-substituted sulfonamides under Mitsunobu reaction conditions (DEAD, PPh₃, THF). The best isolated yields were obtained when N-Boc p-toluenesulfonamide was used as the nitrogen nucleophile precursor in the Mitsunobu reaction. Subsequently, the N-trityl group was efficiently replaced with the more stable allyloxycarbonyl (alloc) group.

Recommended Citation

Kelleher, F. and O'Proinsias, K. Use of the Mitsunobu reaction in the synthesis of orthogonally protected a,b-diaminopropionic acids. Tetrahedron Letters, 48(28):4879-4882. DOI:10.1016/j.tetlet.2007.05.064

Funder

Irish Government