Organocatalytic diastereo- and enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones.
5-Aryl-1,3-dioxolan-4-one heterocycles derived from mandelic acid derivatives and hexafluoroacetone have been identified as new and effective pro-nucleophiles in highly diastereo- and enantioselective Michael addition reactions to nitro olefins catalyzed by bifunctional epi-9-amino-9-deoxy cinchona...
| Main Authors: | , , , , |
|---|---|
| Format: | Journal article |
| Language: | English |
| Published: |
2007
|
| _version_ | 1797091287451566080 |
|---|---|
| author | Hynes, P Stranges, D Stupple, P Guarna, A Dixon, D |
| author_facet | Hynes, P Stranges, D Stupple, P Guarna, A Dixon, D |
| author_sort | Hynes, P |
| collection | OXFORD |
| description | 5-Aryl-1,3-dioxolan-4-one heterocycles derived from mandelic acid derivatives and hexafluoroacetone have been identified as new and effective pro-nucleophiles in highly diastereo- and enantioselective Michael addition reactions to nitro olefins catalyzed by bifunctional epi-9-amino-9-deoxy cinchona alkaloid derivatives. Diastereoselectivities up to 98% and enantioselectivities up to 89% for a range of nitro olefins and 5-aryl-1,3-dioxolan-4-ones under mild reaction conditions are reported. |
| first_indexed | 2024-03-07T03:30:49Z |
| format | Journal article |
| id | oxford-uuid:baa67c4e-a1cf-477a-8ff9-34361cbc57e1 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T03:30:49Z |
| publishDate | 2007 |
| record_format | dspace |
| spelling | oxford-uuid:baa67c4e-a1cf-477a-8ff9-34361cbc57e12022-03-27T05:11:18ZOrganocatalytic diastereo- and enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:baa67c4e-a1cf-477a-8ff9-34361cbc57e1EnglishSymplectic Elements at Oxford2007Hynes, PStranges, DStupple, PGuarna, ADixon, D5-Aryl-1,3-dioxolan-4-one heterocycles derived from mandelic acid derivatives and hexafluoroacetone have been identified as new and effective pro-nucleophiles in highly diastereo- and enantioselective Michael addition reactions to nitro olefins catalyzed by bifunctional epi-9-amino-9-deoxy cinchona alkaloid derivatives. Diastereoselectivities up to 98% and enantioselectivities up to 89% for a range of nitro olefins and 5-aryl-1,3-dioxolan-4-ones under mild reaction conditions are reported. |
| spellingShingle | Hynes, P Stranges, D Stupple, P Guarna, A Dixon, D Organocatalytic diastereo- and enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones. |
| title | Organocatalytic diastereo- and enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones. |
| title_full | Organocatalytic diastereo- and enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones. |
| title_fullStr | Organocatalytic diastereo- and enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones. |
| title_full_unstemmed | Organocatalytic diastereo- and enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones. |
| title_short | Organocatalytic diastereo- and enantioselective Michael addition reactions of 5-aryl-1,3-dioxolan-4-ones. |
| title_sort | organocatalytic diastereo and enantioselective michael addition reactions of 5 aryl 1 3 dioxolan 4 ones |
| work_keys_str_mv | AT hynesp organocatalyticdiastereoandenantioselectivemichaeladditionreactionsof5aryl13dioxolan4ones AT strangesd organocatalyticdiastereoandenantioselectivemichaeladditionreactionsof5aryl13dioxolan4ones AT stupplep organocatalyticdiastereoandenantioselectivemichaeladditionreactionsof5aryl13dioxolan4ones AT guarnaa organocatalyticdiastereoandenantioselectivemichaeladditionreactionsof5aryl13dioxolan4ones AT dixond organocatalyticdiastereoandenantioselectivemichaeladditionreactionsof5aryl13dioxolan4ones |