Fischer, Sebastian and Nguyen, Terrence-Thang H. and Ratzenboeck, Andreas and Davies, Huw M. L. and Reiser, Oliver (2023) Stereoselective Synthesis of Highly Functionalized Cyclohexenes via Strong-Acid-Mediated Endocyclic C-C Bond Cleavage of Monocyclopropanated Cyclopentadienes. ORGANIC LETTERS, 25 (24). pp. 4411-4415. ISSN 1523-7060, 1523-7052
Full text not available from this repository. (Request a copy)Abstract
A stereoselective,solvent- and metal-free endocyclic C-Cbond cleavage of monocyclopropanated cyclopentadienes mediated bystrong acids was developed, leading to highly functionalized six-memberedcarbocycles with high stereocontrol. The critical step for this ring-expansionis the formation of a cyclopropyl carbocation that undergoes endocyclicring opening via an SN2 '-type attack of variousnucleophiles. Subsequent synthetic transformations show the versatilityof the resulting cyclohexenes for the synthesis of new compounds withnonconventional substitution patterns.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | RING-EXPANSION; CYCLOPROPANES; REARRANGEMENT; SOLVOLYSIS; CHEMISTRY |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 13 Mar 2024 10:01 |
| Last Modified: | 13 Mar 2024 10:01 |
| URI: | https://pred.uni-regensburg.de/id/eprint/59541 |
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