Asymmetric synthesis of beta-pyridyl-beta-amino acid derivatives
The conjugate additions of homochiral lithium (R)-N-benzyl-N-α-methyl-4-methoxybenzylamide to tert-butyl 3-(3-pyridyl)- and tert-butyl 3-(4-pyridyl)-prop-2-enoates proceed in 84% de, and after subsequent recrystallisation and oxidative N-deprotection furnish the (S)-3-(3-pyridyl)- and (S)-3-(4-pyrid...
| Main Authors: | , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2002
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| _version_ | 1797099319239639040 |
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| author | Bull, S Davies, S Fox, D Gianotti, M Kelly, P Pierres, C Savory, E Smith, A |
| author_facet | Bull, S Davies, S Fox, D Gianotti, M Kelly, P Pierres, C Savory, E Smith, A |
| author_sort | Bull, S |
| collection | OXFORD |
| description | The conjugate additions of homochiral lithium (R)-N-benzyl-N-α-methyl-4-methoxybenzylamide to tert-butyl 3-(3-pyridyl)- and tert-butyl 3-(4-pyridyl)-prop-2-enoates proceed in 84% de, and after subsequent recrystallisation and oxidative N-deprotection furnish the (S)-3-(3-pyridyl)- and (S)-3-(4-pyridyl)-β-amino acid derivatives in 97% ee and 98% ee respectively. Conjugate additions of lithium N-benzyl-N-α-methyl-4-methoxybenzylamide to tert-butyl 3-(2-pyridyl)prop-2-enoates proceed with low levels of diastereoselectivity unless the 3-(2-pyridyl) ring is substituted. Application of this methodology allows the asymmetric synthesis of (R)-tert-butyl 3-(2-chloro-3-methoxymethoxy-6-pyridyl)-3-aminopropanoate, the protected β-amino ester component of kedarcidin, in 97% ee. |
| first_indexed | 2024-03-07T05:22:07Z |
| format | Journal article |
| id | oxford-uuid:df478445-e7da-4f8b-9cb1-647fd50b962f |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T05:22:07Z |
| publishDate | 2002 |
| record_format | dspace |
| spelling | oxford-uuid:df478445-e7da-4f8b-9cb1-647fd50b962f2022-03-27T09:38:17ZAsymmetric synthesis of beta-pyridyl-beta-amino acid derivativesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:df478445-e7da-4f8b-9cb1-647fd50b962fEnglishSymplectic Elements at Oxford2002Bull, SDavies, SFox, DGianotti, MKelly, PPierres, CSavory, ESmith, AThe conjugate additions of homochiral lithium (R)-N-benzyl-N-α-methyl-4-methoxybenzylamide to tert-butyl 3-(3-pyridyl)- and tert-butyl 3-(4-pyridyl)-prop-2-enoates proceed in 84% de, and after subsequent recrystallisation and oxidative N-deprotection furnish the (S)-3-(3-pyridyl)- and (S)-3-(4-pyridyl)-β-amino acid derivatives in 97% ee and 98% ee respectively. Conjugate additions of lithium N-benzyl-N-α-methyl-4-methoxybenzylamide to tert-butyl 3-(2-pyridyl)prop-2-enoates proceed with low levels of diastereoselectivity unless the 3-(2-pyridyl) ring is substituted. Application of this methodology allows the asymmetric synthesis of (R)-tert-butyl 3-(2-chloro-3-methoxymethoxy-6-pyridyl)-3-aminopropanoate, the protected β-amino ester component of kedarcidin, in 97% ee. |
| spellingShingle | Bull, S Davies, S Fox, D Gianotti, M Kelly, P Pierres, C Savory, E Smith, A Asymmetric synthesis of beta-pyridyl-beta-amino acid derivatives |
| title | Asymmetric synthesis of beta-pyridyl-beta-amino acid derivatives |
| title_full | Asymmetric synthesis of beta-pyridyl-beta-amino acid derivatives |
| title_fullStr | Asymmetric synthesis of beta-pyridyl-beta-amino acid derivatives |
| title_full_unstemmed | Asymmetric synthesis of beta-pyridyl-beta-amino acid derivatives |
| title_short | Asymmetric synthesis of beta-pyridyl-beta-amino acid derivatives |
| title_sort | asymmetric synthesis of beta pyridyl beta amino acid derivatives |
| work_keys_str_mv | AT bulls asymmetricsynthesisofbetapyridylbetaaminoacidderivatives AT daviess asymmetricsynthesisofbetapyridylbetaaminoacidderivatives AT foxd asymmetricsynthesisofbetapyridylbetaaminoacidderivatives AT gianottim asymmetricsynthesisofbetapyridylbetaaminoacidderivatives AT kellyp asymmetricsynthesisofbetapyridylbetaaminoacidderivatives AT pierresc asymmetricsynthesisofbetapyridylbetaaminoacidderivatives AT savorye asymmetricsynthesisofbetapyridylbetaaminoacidderivatives AT smitha asymmetricsynthesisofbetapyridylbetaaminoacidderivatives |