Cyclizations of Silyl Enol Ether Radical Cations− The Cause of the Stereoselectivity
| Autor: | Birka Hein, Eike K. Heilmann, Jens O. Bunte, Jochen Mattay |
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| Rok vydání: | 2004 |
| Předmět: |
Silylation
radical cation silyl enol ether Organic Chemistry Reactive intermediate Silyl enol ether density functional calculation stereoselectivity electron transfer Photochemistry Medicinal chemistry Enol Photoinduced electron transfer chemistry.chemical_compound Electron transfer chemistry Radical ion Stereoselectivity Physical and Theoretical Chemistry |
| Zdroj: | European Journal of Organic Chemistry. 2004:3535-3550 |
| ISSN: | 1099-0690 1434-193X |
| DOI: | 10.1002/ejoc.200400128 |
| Popis: | We have used photoinduced electron transfer (PET) activation of silyl enol ethers for the synthesis of tricyclic hydrocarbons. The mechanism of this reaction was investigated by conducting independent radical-induced cyclizations of corresponding iodo ketones and performing density functional theory (DFT) calculations on the possible intermediates. Our aim was to explain the nature of the reactive intermediate of the cyclization step and to find the causes of the various types of selectivity observed in this process. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004. |
| Databáze: | OpenAIRE |
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