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

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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.

    Creators(s): Watson, Morag E. ORCID logoORCID: https://orcid.org/0000-0003-0368-7648, Jamieson, Craig ORCID logoORCID: https://orcid.org/0000-0002-6567-8272, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Mason, Andrew M.;
    Item type:Article
    ID code:69309
    Keywords:amino acids, chiral auxiliary, peptide staples, Chemistry, Chemistry(all)
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Strategic Research Themes > Health and Wellbeing
    Depositing user: Pure Administrator
    Date deposited:12 Aug 2019 14:15
    Last modified:10 Sep 2020 03:08
    URI:https://strathprints.strath.ac.uk/id/eprint/69309
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