Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements.
Asymmetric [3,3]-sigmatropic aza-Claisen rearrangement of the (Z)-N-allyl-N,O-silylketene aminal of (3S,4E,alphaR)-1-benzyloxy-3-(N-propionyl-N-alpha-methylbenzylamino)hex-4-ene furnishes (2S,3R,4E,alphaR)-N-alpha-methylbenzyl-2,3-dimethyl-7-benzyloxyhept-4-enamide in > 92% d.e.; rearrangemen...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2003
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| _version_ | 1826301131977916416 |
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| author | Davies, S Garner, A Nicholson, R Osborne, J Savory, E Smith, A |
| author_facet | Davies, S Garner, A Nicholson, R Osborne, J Savory, E Smith, A |
| author_sort | Davies, S |
| collection | OXFORD |
| description | Asymmetric [3,3]-sigmatropic aza-Claisen rearrangement of the (Z)-N-allyl-N,O-silylketene aminal of (3S,4E,alphaR)-1-benzyloxy-3-(N-propionyl-N-alpha-methylbenzylamino)hex-4-ene furnishes (2S,3R,4E,alphaR)-N-alpha-methylbenzyl-2,3-dimethyl-7-benzyloxyhept-4-enamide in > 92% d.e.; rearrangement of the diastereomeric (3R,4E,alphaR)-(Z)-N,O-silylketene aminal proceeds with low diastereoselectivity. |
| first_indexed | 2024-03-07T05:27:45Z |
| format | Journal article |
| id | oxford-uuid:e12575f7-1bdd-402c-874f-9bd274e34ad1 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:27:45Z |
| publishDate | 2003 |
| record_format | dspace |
| spelling | oxford-uuid:e12575f7-1bdd-402c-874f-9bd274e34ad12022-03-27T09:52:22ZDouble diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:e12575f7-1bdd-402c-874f-9bd274e34ad1EnglishSymplectic Elements at Oxford2003Davies, SGarner, ANicholson, ROsborne, JSavory, ESmith, AAsymmetric [3,3]-sigmatropic aza-Claisen rearrangement of the (Z)-N-allyl-N,O-silylketene aminal of (3S,4E,alphaR)-1-benzyloxy-3-(N-propionyl-N-alpha-methylbenzylamino)hex-4-ene furnishes (2S,3R,4E,alphaR)-N-alpha-methylbenzyl-2,3-dimethyl-7-benzyloxyhept-4-enamide in > 92% d.e.; rearrangement of the diastereomeric (3R,4E,alphaR)-(Z)-N,O-silylketene aminal proceeds with low diastereoselectivity. |
| spellingShingle | Davies, S Garner, A Nicholson, R Osborne, J Savory, E Smith, A Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. |
| title | Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. |
| title_full | Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. |
| title_fullStr | Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. |
| title_full_unstemmed | Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. |
| title_short | Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements. |
| title_sort | double diastereoselective 3 3 sigmatropic aza claisen rearrangements |
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