Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements.
The doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangement of silylketene aminals derived from 5-substituted (3S,4E,alphaR)-1-benzyloxy-3-[N-acyl-N-(alpha-methylbenzyl)amino]pent-4-enes furnishes 2,3-disubstituted (R)-N-alpha-methylbenzyl (2S,3R,4E)-7-benzyloxyhept-4-enamides in &...
| Main Authors: | , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2009
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| _version_ | 1797097712322084864 |
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| author | Davies, S Garner, A Nicholson, R Osborne, J Roberts, P Savory, E Smith, A Thomson, J |
| author_facet | Davies, S Garner, A Nicholson, R Osborne, J Roberts, P Savory, E Smith, A Thomson, J |
| author_sort | Davies, S |
| collection | OXFORD |
| description | The doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangement of silylketene aminals derived from 5-substituted (3S,4E,alphaR)-1-benzyloxy-3-[N-acyl-N-(alpha-methylbenzyl)amino]pent-4-enes furnishes 2,3-disubstituted (R)-N-alpha-methylbenzyl (2S,3R,4E)-7-benzyloxyhept-4-enamides in >90% de under the "matched" control of both stereogenic centres. Rearrangement of the "mismatched" diastereomeric (3R,4E,alphaR)-substrates proceeds with low diastereoselectivity. The substrate scope of the doubly diastereoselective rearrangement of the "matched" substrates in which two new stereogenic centres are created has been delineated. |
| first_indexed | 2024-03-07T04:59:25Z |
| format | Journal article |
| id | oxford-uuid:d7c1b761-6353-4263-a276-fc654f14a5c4 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:59:25Z |
| publishDate | 2009 |
| record_format | dspace |
| spelling | oxford-uuid:d7c1b761-6353-4263-a276-fc654f14a5c42022-03-27T08:43:24ZDoubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:d7c1b761-6353-4263-a276-fc654f14a5c4EnglishSymplectic Elements at Oxford2009Davies, SGarner, ANicholson, ROsborne, JRoberts, PSavory, ESmith, AThomson, JThe doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangement of silylketene aminals derived from 5-substituted (3S,4E,alphaR)-1-benzyloxy-3-[N-acyl-N-(alpha-methylbenzyl)amino]pent-4-enes furnishes 2,3-disubstituted (R)-N-alpha-methylbenzyl (2S,3R,4E)-7-benzyloxyhept-4-enamides in >90% de under the "matched" control of both stereogenic centres. Rearrangement of the "mismatched" diastereomeric (3R,4E,alphaR)-substrates proceeds with low diastereoselectivity. The substrate scope of the doubly diastereoselective rearrangement of the "matched" substrates in which two new stereogenic centres are created has been delineated. |
| spellingShingle | Davies, S Garner, A Nicholson, R Osborne, J Roberts, P Savory, E Smith, A Thomson, J Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. |
| title | Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. |
| title_full | Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. |
| title_fullStr | Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. |
| title_full_unstemmed | Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. |
| title_short | Doubly diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. |
| title_sort | doubly diastereoselective 3 3 sigmatropic aza claisen rearrangements |
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