Ammonium-directed oxidation of cyclic allylic and homoallylic amines.
The ammonium-directed olefinic oxidation of a range of cyclic allylic and homoallylic amines has been investigated. Functionalization of a range of allylic 3-(N,N-dibenzylamino)cycloalk-1-enes with m-CPBA in the presence of Cl(3)CCO(2)H gives exclusively the corresponding syn-epoxide for the 5-membe...
| Main Authors: | , , , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2009
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| _version_ | 1797066266406551552 |
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| author | Bond, C Cresswell, A Davies, S Fletcher, A Kurosawa, W Lee, J Roberts, P Russell, A Smith, A Thomson, J |
| author_facet | Bond, C Cresswell, A Davies, S Fletcher, A Kurosawa, W Lee, J Roberts, P Russell, A Smith, A Thomson, J |
| author_sort | Bond, C |
| collection | OXFORD |
| description | The ammonium-directed olefinic oxidation of a range of cyclic allylic and homoallylic amines has been investigated. Functionalization of a range of allylic 3-(N,N-dibenzylamino)cycloalk-1-enes with m-CPBA in the presence of Cl(3)CCO(2)H gives exclusively the corresponding syn-epoxide for the 5-membered ring (>99:1 dr), the anti-epoxide for the 8-membered ring (>99:1 dr), and predominantly the anti-epoxide for the 7-membered ring (94:6 dr). Oxidation of the homoallylic amines 3-(N-benzylamino)methylcyclohex-1-ene and 3-(N,N-dibenzylamino)methylcyclohex-1-ene gave, in both cases, the corresponding N-protected 1,2-anti-2,3-syn-3-aminomethylcyclohexane-1,2-diol with high levels of diastereoselectivity (>or=90:10 dr). The versatile synthetic intermediates resulting from these oxidation reactions are readily transformed into a range of amino diols. |
| first_indexed | 2024-03-06T21:40:00Z |
| format | Journal article |
| id | oxford-uuid:47970507-fecf-482a-bfba-3b76506a3305 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T21:40:00Z |
| publishDate | 2009 |
| record_format | dspace |
| spelling | oxford-uuid:47970507-fecf-482a-bfba-3b76506a33052022-03-26T15:21:00ZAmmonium-directed oxidation of cyclic allylic and homoallylic amines.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:47970507-fecf-482a-bfba-3b76506a3305EnglishSymplectic Elements at Oxford2009Bond, CCresswell, ADavies, SFletcher, AKurosawa, WLee, JRoberts, PRussell, ASmith, AThomson, JThe ammonium-directed olefinic oxidation of a range of cyclic allylic and homoallylic amines has been investigated. Functionalization of a range of allylic 3-(N,N-dibenzylamino)cycloalk-1-enes with m-CPBA in the presence of Cl(3)CCO(2)H gives exclusively the corresponding syn-epoxide for the 5-membered ring (>99:1 dr), the anti-epoxide for the 8-membered ring (>99:1 dr), and predominantly the anti-epoxide for the 7-membered ring (94:6 dr). Oxidation of the homoallylic amines 3-(N-benzylamino)methylcyclohex-1-ene and 3-(N,N-dibenzylamino)methylcyclohex-1-ene gave, in both cases, the corresponding N-protected 1,2-anti-2,3-syn-3-aminomethylcyclohexane-1,2-diol with high levels of diastereoselectivity (>or=90:10 dr). The versatile synthetic intermediates resulting from these oxidation reactions are readily transformed into a range of amino diols. |
| spellingShingle | Bond, C Cresswell, A Davies, S Fletcher, A Kurosawa, W Lee, J Roberts, P Russell, A Smith, A Thomson, J Ammonium-directed oxidation of cyclic allylic and homoallylic amines. |
| title | Ammonium-directed oxidation of cyclic allylic and homoallylic amines. |
| title_full | Ammonium-directed oxidation of cyclic allylic and homoallylic amines. |
| title_fullStr | Ammonium-directed oxidation of cyclic allylic and homoallylic amines. |
| title_full_unstemmed | Ammonium-directed oxidation of cyclic allylic and homoallylic amines. |
| title_short | Ammonium-directed oxidation of cyclic allylic and homoallylic amines. |
| title_sort | ammonium directed oxidation of cyclic allylic and homoallylic amines |
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