Asymmetric synthesis of cyclic beta-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis
Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters followed by ring closing metathesis is used to afford efficiently a range of substituted cyclic β-amino esters in high d.e. Alternatively, conjugate addition to α,β-unsaturated Wei...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Published: |
2003
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| _version_ | 1797062808886575104 |
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| author | Chippindale, A Davies, S Iwamoto, K Parkin, R Smethurst, C Smith, A Rodriguez-Solla, H |
| author_facet | Chippindale, A Davies, S Iwamoto, K Parkin, R Smethurst, C Smith, A Rodriguez-Solla, H |
| author_sort | Chippindale, A |
| collection | OXFORD |
| description | Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters followed by ring closing metathesis is used to afford efficiently a range of substituted cyclic β-amino esters in high d.e. Alternatively, conjugate addition to α,β-unsaturated Weinreb amides, functional group conversion and ring closing metathesis affords cyclic amines in high d.e. The further application of this methodology to the synthesis of a range of carbocyclic β-amino esters via conjugate addition, enolate alkylation and ring closing metathesis is also described. Application of this methodology affords, after deprotection, (S)-homoproline, (S)-homopipecolic acid, (S)-coniine and (1S,2S)-trans-pentacin. © 2003 Elsevier Science Ltd. All rights reserved. |
| first_indexed | 2024-03-06T20:50:53Z |
| format | Journal article |
| id | oxford-uuid:3787b03c-45bf-4615-8d79-a1506e958501 |
| institution | University of Oxford |
| last_indexed | 2024-03-06T20:50:53Z |
| publishDate | 2003 |
| record_format | dspace |
| spelling | oxford-uuid:3787b03c-45bf-4615-8d79-a1506e9585012022-03-26T13:44:33ZAsymmetric synthesis of cyclic beta-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesisJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:3787b03c-45bf-4615-8d79-a1506e958501Symplectic Elements at Oxford2003Chippindale, ADavies, SIwamoto, KParkin, RSmethurst, CSmith, ARodriguez-Solla, HDiastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters followed by ring closing metathesis is used to afford efficiently a range of substituted cyclic β-amino esters in high d.e. Alternatively, conjugate addition to α,β-unsaturated Weinreb amides, functional group conversion and ring closing metathesis affords cyclic amines in high d.e. The further application of this methodology to the synthesis of a range of carbocyclic β-amino esters via conjugate addition, enolate alkylation and ring closing metathesis is also described. Application of this methodology affords, after deprotection, (S)-homoproline, (S)-homopipecolic acid, (S)-coniine and (1S,2S)-trans-pentacin. © 2003 Elsevier Science Ltd. All rights reserved. |
| spellingShingle | Chippindale, A Davies, S Iwamoto, K Parkin, R Smethurst, C Smith, A Rodriguez-Solla, H Asymmetric synthesis of cyclic beta-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis |
| title | Asymmetric synthesis of cyclic beta-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis |
| title_full | Asymmetric synthesis of cyclic beta-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis |
| title_fullStr | Asymmetric synthesis of cyclic beta-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis |
| title_full_unstemmed | Asymmetric synthesis of cyclic beta-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis |
| title_short | Asymmetric synthesis of cyclic beta-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis |
| title_sort | asymmetric synthesis of cyclic beta amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis |
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