Diastereoselective synthesis and conformational analysis of (2R)- and (2S)-fluorostatines: an approach based on organocatalytic fluorination of a chiral aldehyde

Xiang Guo Hu, Aggie Lawer, Matthew B. Peterson, Hasti Iranmanesh, Graham E. Ball, Luke Hunter*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    20 Citations (Scopus)

    Abstract

    (Chemical Equation Presented). Stereoselectively fluorinated analogues of the amino acid statine have been efficiently synthesized. The key step is an organocatalytic electrophilic fluorination of a chiral β-oxygenated aldehyde, which provided a test of both diastereoselectivity and chemoselectivity. The target statine analogues were found to adopt unique conformations influenced by the fluorine gauche effect, rendering them potentially valuable building blocks for incorporation into bioactive peptides.

    Original languageEnglish
    Pages (from-to)662-665
    Number of pages4
    JournalOrganic Letters
    Volume18
    Issue number4
    DOIs
    Publication statusPublished - 19 Feb 2016

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