N-acyl 'quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis
A novel route to chiral amides through the efficient, non-racemising, cleavage of N-acyl side chains from a 'Quat' chiral auxiliary using N-centred nucleophiles is described. The synthetic utility of the procedure is then highlighted by the preparation of a range of succinamide and succini...
| Main Authors: | , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2002
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| _version_ | 1797087930182795264 |
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| author | Davies, S Dixon, D |
| author_facet | Davies, S Dixon, D |
| author_sort | Davies, S |
| collection | OXFORD |
| description | A novel route to chiral amides through the efficient, non-racemising, cleavage of N-acyl side chains from a 'Quat' chiral auxiliary using N-centred nucleophiles is described. The synthetic utility of the procedure is then highlighted by the preparation of a range of succinamide and succinimide derivatives and through the synthesis of the natural product (S)-(+)-amphetamine via a stereospecific Hofman type degradation using a hypervalent iodine reagent. |
| first_indexed | 2024-03-07T02:42:35Z |
| format | Journal article |
| id | oxford-uuid:aaf39900-b09d-4b0c-a8a3-c7edf17b8763 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T02:42:35Z |
| publishDate | 2002 |
| record_format | dspace |
| spelling | oxford-uuid:aaf39900-b09d-4b0c-a8a3-c7edf17b87632022-03-27T03:18:40ZN-acyl 'quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysisJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:aaf39900-b09d-4b0c-a8a3-c7edf17b8763EnglishSymplectic Elements at Oxford2002Davies, SDixon, DA novel route to chiral amides through the efficient, non-racemising, cleavage of N-acyl side chains from a 'Quat' chiral auxiliary using N-centred nucleophiles is described. The synthetic utility of the procedure is then highlighted by the preparation of a range of succinamide and succinimide derivatives and through the synthesis of the natural product (S)-(+)-amphetamine via a stereospecific Hofman type degradation using a hypervalent iodine reagent. |
| spellingShingle | Davies, S Dixon, D N-acyl 'quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis |
| title | N-acyl 'quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis |
| title_full | N-acyl 'quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis |
| title_fullStr | N-acyl 'quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis |
| title_full_unstemmed | N-acyl 'quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis |
| title_short | N-acyl 'quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis |
| title_sort | n acyl quat pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis |
| work_keys_str_mv | AT daviess nacylquatpyrrolidinoneauxiliaryasachiralamideequivalentviadirectaminolysis AT dixond nacylquatpyrrolidinoneauxiliaryasachiralamideequivalentviadirectaminolysis |