Enantioselective organocatalytic aldol reaction of ynones and its synthetic applications.
[Structure: see text] For the first time, unmodified ynones were used in organocatalytic asymmetric aldol reactions delivering monoprotected anti-alpha,beta-dihydroxyynones in high yields, dr's up to 19:1, and ee's up to 95%. These products can be either reduced to afford enantioenriched u...
| Autores principales: | , , |
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| Formato: | Journal article |
| Lenguaje: | English |
| Publicado: |
2006
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| _version_ | 1826279989361770496 |
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| author | Silva, F Sawicki, M Gouverneur, V |
| author_facet | Silva, F Sawicki, M Gouverneur, V |
| author_sort | Silva, F |
| collection | OXFORD |
| description | [Structure: see text] For the first time, unmodified ynones were used in organocatalytic asymmetric aldol reactions delivering monoprotected anti-alpha,beta-dihydroxyynones in high yields, dr's up to 19:1, and ee's up to 95%. These products can be either reduced to afford enantioenriched unsaturated anti,anti-triol or cyclized using a novel intramolecular phosphine-catalyzed alpha-addition to the ynone. This organocatalytic sequential aldol-cyclization process provides a concise entry to unusual enantioenriched oxygenated heterocycles, which can be used for subsequent structural manipulations. |
| first_indexed | 2024-03-07T00:07:02Z |
| format | Journal article |
| id | oxford-uuid:77e3472c-34ec-4569-83d5-66f60d9e898b |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T00:07:02Z |
| publishDate | 2006 |
| record_format | dspace |
| spelling | oxford-uuid:77e3472c-34ec-4569-83d5-66f60d9e898b2022-03-26T20:27:07ZEnantioselective organocatalytic aldol reaction of ynones and its synthetic applications.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:77e3472c-34ec-4569-83d5-66f60d9e898bEnglishSymplectic Elements at Oxford2006Silva, FSawicki, MGouverneur, V[Structure: see text] For the first time, unmodified ynones were used in organocatalytic asymmetric aldol reactions delivering monoprotected anti-alpha,beta-dihydroxyynones in high yields, dr's up to 19:1, and ee's up to 95%. These products can be either reduced to afford enantioenriched unsaturated anti,anti-triol or cyclized using a novel intramolecular phosphine-catalyzed alpha-addition to the ynone. This organocatalytic sequential aldol-cyclization process provides a concise entry to unusual enantioenriched oxygenated heterocycles, which can be used for subsequent structural manipulations. |
| spellingShingle | Silva, F Sawicki, M Gouverneur, V Enantioselective organocatalytic aldol reaction of ynones and its synthetic applications. |
| title | Enantioselective organocatalytic aldol reaction of ynones and its synthetic applications. |
| title_full | Enantioselective organocatalytic aldol reaction of ynones and its synthetic applications. |
| title_fullStr | Enantioselective organocatalytic aldol reaction of ynones and its synthetic applications. |
| title_full_unstemmed | Enantioselective organocatalytic aldol reaction of ynones and its synthetic applications. |
| title_short | Enantioselective organocatalytic aldol reaction of ynones and its synthetic applications. |
| title_sort | enantioselective organocatalytic aldol reaction of ynones and its synthetic applications |
| work_keys_str_mv | AT silvaf enantioselectiveorganocatalyticaldolreactionofynonesanditssyntheticapplications AT sawickim enantioselectiveorganocatalyticaldolreactionofynonesanditssyntheticapplications AT gouverneurv enantioselectiveorganocatalyticaldolreactionofynonesanditssyntheticapplications |