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Fluorine‐Directed Diastereoselective Iodocyclizations
Author(s) -
Tredwell Matthew,
Luft Jennifer A. R.,
Schuler Marie,
Tenza Kenny,
Houk Kendall N.,
Gouverneur Véronique
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200703465
Subject(s) - substituent , allylic rearrangement , fluorine , closure (psychology) , ring (chemistry) , computer science , chemistry , content (measure theory) , group (periodic table) , work (physics) , organic chemistry , mathematics , political science , catalysis , physics , thermodynamics , law , mathematical analysis
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.