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Fluorine-directed diastereoselective iodocyclizations

Tredwell, Matthew ORCID:, Luft, Jennifer A R, Schuler, Marie, Tenza, Kenny, Houk, Kendall N and Gouverneur, Veronique 2008. Fluorine-directed diastereoselective iodocyclizations. Angewandte Chemie International Edition 47 (2) , pp. 357-360. 10.1002/anie.200703465

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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.

Item Type: Article
Status: Published
Schools: Medicine
Publisher: Wiley
ISSN: 1433-7851
Last Modified: 04 Nov 2022 12:12

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