Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins.
The diastereoselective Ireland-Claisen rearrangement of a range of substituted allyl β-amino esters gave the corresponding enantiopure α-substituted-β-amino esters with good diastereoselectivity. The application of this methodology in the asymmetric synthesis of a range of C(5)-substituted 1,2-anti-...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2014
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| _version_ | 1826299099507326976 |
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| author | Davies, S Fletcher, A Lee, J Roberts, P Souleymanou, M Thomson, J Zammit, C |
| author_facet | Davies, S Fletcher, A Lee, J Roberts, P Souleymanou, M Thomson, J Zammit, C |
| author_sort | Davies, S |
| collection | OXFORD |
| description | The diastereoselective Ireland-Claisen rearrangement of a range of substituted allyl β-amino esters gave the corresponding enantiopure α-substituted-β-amino esters with good diastereoselectivity. The application of this methodology in the asymmetric synthesis of a range of C(5)-substituted 1,2-anti-1,5-syn-transpentacins was demonstrated by the rearrangement of a range of β-amino esters derived from sorbic acid, followed by esterification, ring-closing metathesis, hydrogenolytic deprotection/reduction, and hydrolysis, which gave the C(5)-substituted transpentacins in only 9 steps from commercially available starting materials. |
| first_indexed | 2024-03-07T04:56:46Z |
| format | Journal article |
| id | oxford-uuid:d6ddf9a6-6447-4d98-85d1-d7661a4828fe |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:56:46Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | oxford-uuid:d6ddf9a6-6447-4d98-85d1-d7661a4828fe2022-03-27T08:36:47ZDiastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:d6ddf9a6-6447-4d98-85d1-d7661a4828feEnglishSymplectic Elements at Oxford2014Davies, SFletcher, ALee, JRoberts, PSouleymanou, MThomson, JZammit, CThe diastereoselective Ireland-Claisen rearrangement of a range of substituted allyl β-amino esters gave the corresponding enantiopure α-substituted-β-amino esters with good diastereoselectivity. The application of this methodology in the asymmetric synthesis of a range of C(5)-substituted 1,2-anti-1,5-syn-transpentacins was demonstrated by the rearrangement of a range of β-amino esters derived from sorbic acid, followed by esterification, ring-closing metathesis, hydrogenolytic deprotection/reduction, and hydrolysis, which gave the C(5)-substituted transpentacins in only 9 steps from commercially available starting materials. |
| spellingShingle | Davies, S Fletcher, A Lee, J Roberts, P Souleymanou, M Thomson, J Zammit, C Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins. |
| title | Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins. |
| title_full | Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins. |
| title_fullStr | Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins. |
| title_full_unstemmed | Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins. |
| title_short | Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins. |
| title_sort | diastereoselective ireland claisen rearrangements of substituted allyl β amino esters applications in the asymmetric synthesis of c 5 substituted transpentacins |
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