Fluorine‐Directed Diastereoselective Iodocyclizations

Abstract

An inside job: β-Fluorinated lactones and tetrahydrofurans are synthesized by iodocyclization of various allylic fluorides. The fluorine substituent acts as a highly efficient syn-stereodirecting group for the ring closure. The experimental results combined with theoretical studies provide evidence in support of an “inside fluoro effect” to account for the sense and level of stereocontrol of these reactions. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z703465_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.