Palladium(0)/indium iodide-mediated allylations of electrophiles generated from the hydrolysis of Eschenmoser’s salt: one-pot preparation of diverse carbocyclic scaffolds
| Autor: | Cara Cesario, Marvin J. Miller |
|---|---|
| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
organic chemicals Organic Chemistry Iodide food and beverages chemistry.chemical_element Biochemistry Article chemistry.chemical_compound Enantiopure drug chemistry Allyl acetate Drug Discovery Eschenmoser's salt Electrophile Organic chemistry Cyclopentene Hydroxymethyl Palladium |
| Zdroj: | Tetrahedron Letters. 51:3050-3052 |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/j.tetlet.2010.04.007 |
| Popis: | A formyl equivalent was generated in situ from Eschenmoser’s salt in aqueous THF and was reacted with an allylindium species. Acylnitroso-derived hetero-Diels Alder adducts and related allyl acetates were shown to be substrates for Pd(0)/InI-mediated allylations of formaldehyde-related species to provide homoallylic alcohols. Hydroxymethyl groups were installed with regio- and diastereocontrol to provide relevant disubstituted carbocyclic scaffolds. Enantiopure anti-disubstituted cyclopentene products were prepared from a chiral allyl acetate. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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