Functionalised bicyclic alcohols by enantioselective alpha-deprotonation-rearrangement of meso-epoxides
Enantioselective α-deprotonation-rearrangement of achiral substituted cyclooctene oxides 7, 27 and 28 and N-Boc hexahydroazonine oxide 45 using organolithiums in the presence of (-)-sparteine 3 or (-)-α-isosparteine 4 gives the functionalised bicyclo[3.3.0]octan-2-ols 9, 29, and 32 and indolizinol 4...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
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2001
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| _version_ | 1797087970750103552 |
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| author | Hodgson, D Cameron, I Christlieb, M Green, R Lee, G Robinson, L |
| author_facet | Hodgson, D Cameron, I Christlieb, M Green, R Lee, G Robinson, L |
| author_sort | Hodgson, D |
| collection | OXFORD |
| description | Enantioselective α-deprotonation-rearrangement of achiral substituted cyclooctene oxides 7, 27 and 28 and N-Boc hexahydroazonine oxide 45 using organolithiums in the presence of (-)-sparteine 3 or (-)-α-isosparteine 4 gives the functionalised bicyclo[3.3.0]octan-2-ols 9, 29, and 32 and indolizinol 47 in 50-72% yields and 83-89% ees. |
| first_indexed | 2024-03-07T02:43:11Z |
| format | Journal article |
| id | oxford-uuid:ab2698f1-910d-409c-9aad-8c00bdf0ed62 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T02:43:11Z |
| publishDate | 2001 |
| record_format | dspace |
| spelling | oxford-uuid:ab2698f1-910d-409c-9aad-8c00bdf0ed622022-03-27T03:19:57ZFunctionalised bicyclic alcohols by enantioselective alpha-deprotonation-rearrangement of meso-epoxidesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:ab2698f1-910d-409c-9aad-8c00bdf0ed62EnglishSymplectic Elements at Oxford2001Hodgson, DCameron, IChristlieb, MGreen, RLee, GRobinson, LEnantioselective α-deprotonation-rearrangement of achiral substituted cyclooctene oxides 7, 27 and 28 and N-Boc hexahydroazonine oxide 45 using organolithiums in the presence of (-)-sparteine 3 or (-)-α-isosparteine 4 gives the functionalised bicyclo[3.3.0]octan-2-ols 9, 29, and 32 and indolizinol 47 in 50-72% yields and 83-89% ees. |
| spellingShingle | Hodgson, D Cameron, I Christlieb, M Green, R Lee, G Robinson, L Functionalised bicyclic alcohols by enantioselective alpha-deprotonation-rearrangement of meso-epoxides |
| title | Functionalised bicyclic alcohols by enantioselective alpha-deprotonation-rearrangement of meso-epoxides |
| title_full | Functionalised bicyclic alcohols by enantioselective alpha-deprotonation-rearrangement of meso-epoxides |
| title_fullStr | Functionalised bicyclic alcohols by enantioselective alpha-deprotonation-rearrangement of meso-epoxides |
| title_full_unstemmed | Functionalised bicyclic alcohols by enantioselective alpha-deprotonation-rearrangement of meso-epoxides |
| title_short | Functionalised bicyclic alcohols by enantioselective alpha-deprotonation-rearrangement of meso-epoxides |
| title_sort | functionalised bicyclic alcohols by enantioselective alpha deprotonation rearrangement of meso epoxides |
| work_keys_str_mv | AT hodgsond functionalisedbicyclicalcoholsbyenantioselectivealphadeprotonationrearrangementofmesoepoxides AT cameroni functionalisedbicyclicalcoholsbyenantioselectivealphadeprotonationrearrangementofmesoepoxides AT christliebm functionalisedbicyclicalcoholsbyenantioselectivealphadeprotonationrearrangementofmesoepoxides AT greenr functionalisedbicyclicalcoholsbyenantioselectivealphadeprotonationrearrangementofmesoepoxides AT leeg functionalisedbicyclicalcoholsbyenantioselectivealphadeprotonationrearrangementofmesoepoxides AT robinsonl functionalisedbicyclicalcoholsbyenantioselectivealphadeprotonationrearrangementofmesoepoxides |