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Use of the Mitsunobu Reaction in the Synthesis of Orthogonally Protected a,b-Diaminopropionic Acids
Kelleher, Fintan; Ó Proinsias, Keith
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.
Keyword(s): diaminopropanoic acids; Mitsunobu reaction; Organic Chemistry
Publication Date:
2007
Type: Other
Peer-Reviewed: Unknown
Contributor(s): Irish Government; PRTLI III
Institution: Dublin Institute of Technology
Citation(s): Articles
Publisher(s): Dublin Institute of Technology
File Format(s): application/pdf
First Indexed: 2013-10-16 05:52:26 Last Updated: 2017-12-14 06:57:24