Tethered Silanoxyiodination of Alkenes
| Autor: | Anand H. Shinde, Ranjeet A. Dhokale, Shyam Sathyamoorthi, Joel T. Mague, Frederick J. Seidl |
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| Rok vydání: | 2021 |
| Předmět: |
Allylic rearrangement
010405 organic chemistry Organic Chemistry Synthon Epoxide Regioselectivity Alkenes 010402 general chemistry 01 natural sciences Combinatorial chemistry Article Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Yield (chemistry) Epoxy Compounds Organic synthesis Selectivity |
| Zdroj: | J Org Chem |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | We present the first examples of tethered silanoxyiodination reactions of allylic alcohols. The products are usefulsilanediol organoiodide synthons and are formed with high regioselectivity and diastereocontrol. The reaction is scalable greater than 10-fold without loss of yield or selectivity. Furthermore, the products are starting materials for further transformations, including de-iodination, C–N bond installation, epoxide synthesis, and de-silylation. DFT calculations provide a basis for understanding the exquisite 6-endo selectivity of this silanoxyiodination reaction and show that the observed products are both kinetically and thermodynamically preferred. |
| Databáze: | OpenAIRE |
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