ASYMMETRIC-SYNTHESIS OF SYN-ALPHA-ALKYL-BETA-AMINO ACIDS
An investigation into the reactivity of the highly stereoselective conjugate nucleophile lithium N-benzyl-N-α-methylbenzylamide 1 with α-alkyl-α,β-unsaturated esters has led to the development of a versatile asymmetric synthesis of syn-α-alkyl-β-amino acids. By performing the conjugate additions in...
| Hoofdauteurs: | , , |
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| Formaat: | Journal article |
| Gepubliceerd in: |
1994
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| _version_ | 1826263316538851328 |
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| author | Davies, S Ichihara, O Walters, I |
| author_facet | Davies, S Ichihara, O Walters, I |
| author_sort | Davies, S |
| collection | OXFORD |
| description | An investigation into the reactivity of the highly stereoselective conjugate nucleophile lithium N-benzyl-N-α-methylbenzylamide 1 with α-alkyl-α,β-unsaturated esters has led to the development of a versatile asymmetric synthesis of syn-α-alkyl-β-amino acids. By performing the conjugate additions in toluene and diluting the reaction mixtures with THF prior to quenching of the reactions with the hindered acid. 2,6-di-tert-butylphenol 13, the product syn-α-alkyl-β-amino esters may be generated in good yield and with excellent stereocontrol. Several examples illustrate the ease with which these products may be debenzylated and hydrolysed to afford homochiral syn-α-alkyl-β-amino acids. |
| first_indexed | 2024-03-06T19:49:49Z |
| format | Journal article |
| id | oxford-uuid:2396e4f2-242b-4d8c-bd0b-0252c356f6ac |
| institution | University of Oxford |
| last_indexed | 2024-03-06T19:49:49Z |
| publishDate | 1994 |
| record_format | dspace |
| spelling | oxford-uuid:2396e4f2-242b-4d8c-bd0b-0252c356f6ac2022-03-26T11:45:01ZASYMMETRIC-SYNTHESIS OF SYN-ALPHA-ALKYL-BETA-AMINO ACIDSJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:2396e4f2-242b-4d8c-bd0b-0252c356f6acSymplectic Elements at Oxford1994Davies, SIchihara, OWalters, IAn investigation into the reactivity of the highly stereoselective conjugate nucleophile lithium N-benzyl-N-α-methylbenzylamide 1 with α-alkyl-α,β-unsaturated esters has led to the development of a versatile asymmetric synthesis of syn-α-alkyl-β-amino acids. By performing the conjugate additions in toluene and diluting the reaction mixtures with THF prior to quenching of the reactions with the hindered acid. 2,6-di-tert-butylphenol 13, the product syn-α-alkyl-β-amino esters may be generated in good yield and with excellent stereocontrol. Several examples illustrate the ease with which these products may be debenzylated and hydrolysed to afford homochiral syn-α-alkyl-β-amino acids. |
| spellingShingle | Davies, S Ichihara, O Walters, I ASYMMETRIC-SYNTHESIS OF SYN-ALPHA-ALKYL-BETA-AMINO ACIDS |
| title | ASYMMETRIC-SYNTHESIS OF SYN-ALPHA-ALKYL-BETA-AMINO ACIDS |
| title_full | ASYMMETRIC-SYNTHESIS OF SYN-ALPHA-ALKYL-BETA-AMINO ACIDS |
| title_fullStr | ASYMMETRIC-SYNTHESIS OF SYN-ALPHA-ALKYL-BETA-AMINO ACIDS |
| title_full_unstemmed | ASYMMETRIC-SYNTHESIS OF SYN-ALPHA-ALKYL-BETA-AMINO ACIDS |
| title_short | ASYMMETRIC-SYNTHESIS OF SYN-ALPHA-ALKYL-BETA-AMINO ACIDS |
| title_sort | asymmetric synthesis of syn alpha alkyl beta amino acids |
| work_keys_str_mv | AT daviess asymmetricsynthesisofsynalphaalkylbetaaminoacids AT ichiharao asymmetricsynthesisofsynalphaalkylbetaaminoacids AT waltersi asymmetricsynthesisofsynalphaalkylbetaaminoacids |