A reappraisal of the Ni-[(Benzylprolyl)amino]benzophenone complex in the synthesis of α,α-disubstituted amino acid derivatives
Watson, Morag E. and Jamieson, Craig and Kennedy, Alan R. and Mason, Andrew M. (2019) A reappraisal of the Ni-[(Benzylprolyl)amino]benzophenone complex in the synthesis of α,α-disubstituted amino acid derivatives. Tetrahedron, 75 (36). 130485. ISSN 0040-4020 (https://doi.org/10.1016/j.tet.2019.130485)
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Abstract
α,α-Disubstituted alkenyl amino acid derivatives (e.g. Fmoc-S 5-OH) are valuable monomers in the construction of stapled peptide derivatives. Synthetic access to these is possible using the Ni-[(Benzylprolyl)amino]benzophenone (BPB) complex as a chiral auxiliary. We discuss a reappraisal of the use of this, and demonstrate that epimerisation of the proline α-centre occurs during formation of the complex, leading to erosion in the enantiomeric excess of the final product. Modified conditions have been developed, providing the target compounds in high enantiomeric excess.
ORCID iDs
Watson, Morag E. ORCID: https://orcid.org/0000-0003-0368-7648, Jamieson, Craig ORCID: https://orcid.org/0000-0002-6567-8272, Kennedy, Alan R. ORCID: https://orcid.org/0000-0003-3652-6015 and Mason, Andrew M.;-
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Item type: Article ID code: 69309 Dates: DateEvent6 September 2019Published27 July 2019Published Online26 July 2019AcceptedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry
Strategic Research Themes > Health and WellbeingDepositing user: Pure Administrator Date deposited: 12 Aug 2019 14:15 Last modified: 03 Oct 2024 00:30 URI: https://strathprints.strath.ac.uk/id/eprint/69309