Highly functionalized cyclic and bicyclic β−amino acids from sugar β−nitroesters
The synthesis of highly functionalized bicyclic and cyclic β-amino acids from β-nitrosugars is reported. Specifically, our strategy for the synthesis of polyhydroxylated cyclopentane β-amino acids via the intramolecular C-alkylation of 6-nitro-2-O-triflates of furanosides has been applied to the pre...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
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Elsevier
2019
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| _version_ | 1797105944310579200 |
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| author | Otero, JM Estévez, AM Estévez, JC Fleet, GWJ Estévez, RJ |
| author_facet | Otero, JM Estévez, AM Estévez, JC Fleet, GWJ Estévez, RJ |
| author_sort | Otero, JM |
| collection | OXFORD |
| description | The synthesis of highly functionalized bicyclic and cyclic β-amino acids from β-nitrosugars is reported. Specifically, our strategy for the synthesis of polyhydroxylated cyclopentane β-amino acids via the intramolecular C-alkylation of 6-nitro-2-O-triflates of furanosides has been applied to the preparation of the first two examples of a novel class of bicyclic β-amino acids and a novel cyclopentene β-amino acid. Also, our Henry reaction mediated strategy for the synthesis of polyhydroxylated cyclohexane β-amino acids has been extended to a divergent, stereoselective synthesis of new polysubstituted cyclohexane and cyclopentane β-amino acids. |
| first_indexed | 2024-03-07T06:54:37Z |
| format | Journal article |
| id | oxford-uuid:fdb52de6-b09d-4afa-964f-48c277e7bab6 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:54:37Z |
| publishDate | 2019 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | oxford-uuid:fdb52de6-b09d-4afa-964f-48c277e7bab62022-03-27T13:30:54ZHighly functionalized cyclic and bicyclic β−amino acids from sugar β−nitroestersJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:fdb52de6-b09d-4afa-964f-48c277e7bab6EnglishSymplectic Elements at OxfordElsevier2019Otero, JMEstévez, AMEstévez, JCFleet, GWJEstévez, RJThe synthesis of highly functionalized bicyclic and cyclic β-amino acids from β-nitrosugars is reported. Specifically, our strategy for the synthesis of polyhydroxylated cyclopentane β-amino acids via the intramolecular C-alkylation of 6-nitro-2-O-triflates of furanosides has been applied to the preparation of the first two examples of a novel class of bicyclic β-amino acids and a novel cyclopentene β-amino acid. Also, our Henry reaction mediated strategy for the synthesis of polyhydroxylated cyclohexane β-amino acids has been extended to a divergent, stereoselective synthesis of new polysubstituted cyclohexane and cyclopentane β-amino acids. |
| spellingShingle | Otero, JM Estévez, AM Estévez, JC Fleet, GWJ Estévez, RJ Highly functionalized cyclic and bicyclic β−amino acids from sugar β−nitroesters |
| title | Highly functionalized cyclic and bicyclic β−amino acids from sugar β−nitroesters |
| title_full | Highly functionalized cyclic and bicyclic β−amino acids from sugar β−nitroesters |
| title_fullStr | Highly functionalized cyclic and bicyclic β−amino acids from sugar β−nitroesters |
| title_full_unstemmed | Highly functionalized cyclic and bicyclic β−amino acids from sugar β−nitroesters |
| title_short | Highly functionalized cyclic and bicyclic β−amino acids from sugar β−nitroesters |
| title_sort | highly functionalized cyclic and bicyclic β amino acids from sugar β nitroesters |
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