Diastereoselective Synthesis and Conformational Analysis of (2<i>R</i>)- and (2<i>S</i>)-Fluorostatines: An Approach Based on Organocatalytic Fluorination of a Chiral Aldehyde

Abstract

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.