1. [6-endo-trig mode cyclization to a hydrindanone using samarium (II) iodide].
- Author
-
Sono M
- Subjects
- Cyclization, Indenes chemical synthesis, Molecular Conformation, Stereoisomerism, Cycloparaffins chemical synthesis, Iodides, Samarium
- Abstract
Samarium (II) iodide has been employed to promote the vinylogous pinacol coupling reaction of aldehyde to alpha, beta-unsaturated ketones. The diastereoselectivity of 6-endo-trig mode products was changed by the addition of a proton source and/or HMPA and by the reaction temperature. The stereochemistry of the hydrindanone was controlled by the coordinated samarium species, resulting in the cis-orientation in respect of the hydroxyl group at C-4 and the juncture proton at C-3a under mild reaction conditions. Coronafacic acid has been synthesized from a hydrindanone prepared by the cyclization reaction of the enone-aldehyde with samarium (II) iodide.
- Published
- 2003
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