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Use Of The Mitsunobu Reaction In The Synthesis Of Orthogonally Protected A,B-Diaminopropionic Acids, Fintan Kelleher, Keith Ó Proinsias

Articles

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.