Radical deoxygenation of 3-azatricyclo[2.2.1.0(2,6)]heptan-5-ols to 2-azabicyclo[2.2.1]hept-5-enes and 1,2-dihydropyridines
Additions of alkyl or aryl Grignard reagents, or pyridin-3-yl-lithiums or lithium alkoxides, to exo-5,6-epoxy-7-(tert-butoxycarbonyl)-2-tosyl-7-azabicyclo[2.2.1]hept-2-ene lead to 7-substituted-1-tosyl-3-azatricyclo[2.2.1.02,6]heptan-5-ols. Radical deoxygenations of 7-alkyl-1-tosyl-3-azatricyclo[2.2...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2009
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| _version_ | 1826296883257016320 |
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| author | Hodgson, D Jones, M Maxwell, C Cowley, A Thompson, A Ichihara, O Matthews, I |
| author_facet | Hodgson, D Jones, M Maxwell, C Cowley, A Thompson, A Ichihara, O Matthews, I |
| author_sort | Hodgson, D |
| collection | OXFORD |
| description | Additions of alkyl or aryl Grignard reagents, or pyridin-3-yl-lithiums or lithium alkoxides, to exo-5,6-epoxy-7-(tert-butoxycarbonyl)-2-tosyl-7-azabicyclo[2.2.1]hept-2-ene lead to 7-substituted-1-tosyl-3-azatricyclo[2.2.1.02,6]heptan-5-ols. Radical deoxygenations of 7-alkyl-1-tosyl-3-azatricyclo[2.2.1.02,6]heptan-5-ols give 7-alkyl-4-tosyl-2-azabicyclo[2.2.1]hept-5-enes, whereas 7-aryl-1-tosyl-3-azatricyclo[2.2.1.02,6]heptan-5-ols give 2-(arylmethyl)-5-tosyl-1,2-dihydropyridines. © 2009 Elsevier Ltd. All rights reserved. |
| first_indexed | 2024-03-07T04:23:11Z |
| format | Journal article |
| id | oxford-uuid:cbb82642-ea96-4727-9b5d-8d3824c5d91f |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:23:11Z |
| publishDate | 2009 |
| record_format | dspace |
| spelling | oxford-uuid:cbb82642-ea96-4727-9b5d-8d3824c5d91f2022-03-27T07:16:49ZRadical deoxygenation of 3-azatricyclo[2.2.1.0(2,6)]heptan-5-ols to 2-azabicyclo[2.2.1]hept-5-enes and 1,2-dihydropyridinesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:cbb82642-ea96-4727-9b5d-8d3824c5d91fEnglishSymplectic Elements at Oxford2009Hodgson, DJones, MMaxwell, CCowley, AThompson, AIchihara, OMatthews, IAdditions of alkyl or aryl Grignard reagents, or pyridin-3-yl-lithiums or lithium alkoxides, to exo-5,6-epoxy-7-(tert-butoxycarbonyl)-2-tosyl-7-azabicyclo[2.2.1]hept-2-ene lead to 7-substituted-1-tosyl-3-azatricyclo[2.2.1.02,6]heptan-5-ols. Radical deoxygenations of 7-alkyl-1-tosyl-3-azatricyclo[2.2.1.02,6]heptan-5-ols give 7-alkyl-4-tosyl-2-azabicyclo[2.2.1]hept-5-enes, whereas 7-aryl-1-tosyl-3-azatricyclo[2.2.1.02,6]heptan-5-ols give 2-(arylmethyl)-5-tosyl-1,2-dihydropyridines. © 2009 Elsevier Ltd. All rights reserved. |
| spellingShingle | Hodgson, D Jones, M Maxwell, C Cowley, A Thompson, A Ichihara, O Matthews, I Radical deoxygenation of 3-azatricyclo[2.2.1.0(2,6)]heptan-5-ols to 2-azabicyclo[2.2.1]hept-5-enes and 1,2-dihydropyridines |
| title | Radical deoxygenation of 3-azatricyclo[2.2.1.0(2,6)]heptan-5-ols to 2-azabicyclo[2.2.1]hept-5-enes and 1,2-dihydropyridines |
| title_full | Radical deoxygenation of 3-azatricyclo[2.2.1.0(2,6)]heptan-5-ols to 2-azabicyclo[2.2.1]hept-5-enes and 1,2-dihydropyridines |
| title_fullStr | Radical deoxygenation of 3-azatricyclo[2.2.1.0(2,6)]heptan-5-ols to 2-azabicyclo[2.2.1]hept-5-enes and 1,2-dihydropyridines |
| title_full_unstemmed | Radical deoxygenation of 3-azatricyclo[2.2.1.0(2,6)]heptan-5-ols to 2-azabicyclo[2.2.1]hept-5-enes and 1,2-dihydropyridines |
| title_short | Radical deoxygenation of 3-azatricyclo[2.2.1.0(2,6)]heptan-5-ols to 2-azabicyclo[2.2.1]hept-5-enes and 1,2-dihydropyridines |
| title_sort | radical deoxygenation of 3 azatricyclo 2 2 1 0 2 6 heptan 5 ols to 2 azabicyclo 2 2 1 hept 5 enes and 1 2 dihydropyridines |
| work_keys_str_mv | AT hodgsond radicaldeoxygenationof3azatricyclo221026heptan5olsto2azabicyclo221hept5enesand12dihydropyridines AT jonesm radicaldeoxygenationof3azatricyclo221026heptan5olsto2azabicyclo221hept5enesand12dihydropyridines AT maxwellc radicaldeoxygenationof3azatricyclo221026heptan5olsto2azabicyclo221hept5enesand12dihydropyridines AT cowleya radicaldeoxygenationof3azatricyclo221026heptan5olsto2azabicyclo221hept5enesand12dihydropyridines AT thompsona radicaldeoxygenationof3azatricyclo221026heptan5olsto2azabicyclo221hept5enesand12dihydropyridines AT ichiharao radicaldeoxygenationof3azatricyclo221026heptan5olsto2azabicyclo221hept5enesand12dihydropyridines AT matthewsi radicaldeoxygenationof3azatricyclo221026heptan5olsto2azabicyclo221hept5enesand12dihydropyridines |