Ammonium-directed dihydroxylation of 3-aminocyclohex-1-enes: development of a metal-free dihydroxylation protocol
| Autor: | Stephen G. Davies, Caroline Aciro, James E. Thomson, Paul M. Roberts, Angela J. Russell, Timothy D. W. Claridge |
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| Jazyk: | angličtina |
| Rok vydání: | 2008 |
| Předmět: |
Allylic rearrangement
Chemistry Organic Chemistry Molecular Conformation Regioselectivity Epoxide Stereoisomerism Hydroxylation Biochemistry Redox Substrate Specificity Quaternary Ammonium Compounds chemistry.chemical_compound Dihydroxylation Metals Cyclohexenes Hydroxides Organic chemistry Ammonium Physical and Theoretical Chemistry Trichloroacetic acid Amines Oxidation-Reduction |
| Zdroj: | Organic and biomolecular chemistry. 6(20) |
| ISSN: | 1477-0539 1477-0520 |
| Popis: | Treatment of 3-aminocyclohex-1-enes with mCPBA in the presence of trichloroacetic acid gives the corresponding 1,2-anti-2,3-syn-1-trichloroacetoxy-2-hydroxy-3-aminocyclohexane with high levels of diastereoselectivity (90% de). This is consistent with a mechanism of oxidation involving hydrogen-bonded delivery of the oxidant by the allylic ammonium ion formed in situ, followed by highly regioselective ring-opening of the intermediate epoxide by trichloroacetic acid. The effect of conformational constraints upon the oxidation reaction is also examined. |
| Databáze: | OpenAIRE |
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