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

17 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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