Selective deprotection strategies to N-(alpha-methylbenzyl)-beta-amino esters and derived beta lactams
A variety of N,N-diprotected β-amino esters, prepared by highly diastereoselective conjugate addition of chiral lithium amides, were selectively mono-deprotected under either reductive (hydrogenolysis) or oxidative (DDQ or CAN) conditions. Combined with these deprotection methods, lithium (α-methylb...
| Main Authors: | , |
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| Format: | Journal article |
| Language: | English |
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1998
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| _version_ | 1826256555702484992 |
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| author | Davies, S Ichihara, O |
| author_facet | Davies, S Ichihara, O |
| author_sort | Davies, S |
| collection | OXFORD |
| description | A variety of N,N-diprotected β-amino esters, prepared by highly diastereoselective conjugate addition of chiral lithium amides, were selectively mono-deprotected under either reductive (hydrogenolysis) or oxidative (DDQ or CAN) conditions. Combined with these deprotection methods, lithium (α-methylbenzyl)(3,4-dimethoxybenzyl) amide 2 can be used as an efficient differentially protected chiral ammonia equivalent for the asymmetric synthesis of β-amino acid and β-lactam derivatives. |
| first_indexed | 2024-03-06T18:04:05Z |
| format | Journal article |
| id | oxford-uuid:00d352cb-b141-4d78-a8e7-a84cd4ce491b |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T18:04:05Z |
| publishDate | 1998 |
| record_format | dspace |
| spelling | oxford-uuid:00d352cb-b141-4d78-a8e7-a84cd4ce491b2022-03-26T08:31:40ZSelective deprotection strategies to N-(alpha-methylbenzyl)-beta-amino esters and derived beta lactamsJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:00d352cb-b141-4d78-a8e7-a84cd4ce491bEnglishSymplectic Elements at Oxford1998Davies, SIchihara, OA variety of N,N-diprotected β-amino esters, prepared by highly diastereoselective conjugate addition of chiral lithium amides, were selectively mono-deprotected under either reductive (hydrogenolysis) or oxidative (DDQ or CAN) conditions. Combined with these deprotection methods, lithium (α-methylbenzyl)(3,4-dimethoxybenzyl) amide 2 can be used as an efficient differentially protected chiral ammonia equivalent for the asymmetric synthesis of β-amino acid and β-lactam derivatives. |
| spellingShingle | Davies, S Ichihara, O Selective deprotection strategies to N-(alpha-methylbenzyl)-beta-amino esters and derived beta lactams |
| title | Selective deprotection strategies to N-(alpha-methylbenzyl)-beta-amino esters and derived beta lactams |
| title_full | Selective deprotection strategies to N-(alpha-methylbenzyl)-beta-amino esters and derived beta lactams |
| title_fullStr | Selective deprotection strategies to N-(alpha-methylbenzyl)-beta-amino esters and derived beta lactams |
| title_full_unstemmed | Selective deprotection strategies to N-(alpha-methylbenzyl)-beta-amino esters and derived beta lactams |
| title_short | Selective deprotection strategies to N-(alpha-methylbenzyl)-beta-amino esters and derived beta lactams |
| title_sort | selective deprotection strategies to n alpha methylbenzyl beta amino esters and derived beta lactams |
| work_keys_str_mv | AT daviess selectivedeprotectionstrategiestonalphamethylbenzylbetaaminoestersandderivedbetalactams AT ichiharao selectivedeprotectionstrategiestonalphamethylbenzylbetaaminoestersandderivedbetalactams |