Fluorine-Directed Diastereoselective Iodocyclizations
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...
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| Veröffentlicht in: | Angewandte Chemie (International ed.) 2008-01, Vol.47 (2), p.357-360 |
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| container_end_page | 360 |
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| container_issue | 2 |
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| container_title | Angewandte Chemie (International ed.) |
| container_volume | 47 |
| creator | Tredwell, Matthew Luft, Jennifer A.R Schuler, Marie Tenza, Kenny Houk, Kendall N Gouverneur, Véronique |
| description | 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. |
| doi_str_mv | 10.1002/anie.200703465 |
| format | Article |
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| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie (International ed.), 2008-01, Vol.47 (2), p.357-360 |
| issn | 1433-7851 1521-3773 |
| language | eng |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Bromine - chemistry Cyclization density functional calculations fluorine Fluorine - chemistry Iodine - chemistry Ions - chemistry lactones Models, Molecular Molecular Structure stereoelectronic effect Stereoisomerism tetrahydrofurans |
| title | Fluorine-Directed Diastereoselective Iodocyclizations |
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