Asymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexes
The synthesis of (SRSs[(phenylsulfinyl)benzene] chromium tricarbonyl 5 and (SRSs)-[(p-tolylsulfiny))benzene] chromium tricarbonyl 6 is achieved via a nucleophilic displacement reaction between the anion derived from (benzene) chromium tricarbonyl 9 and a suitable sulfinate ester. Replacing the sulfi...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
1999
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| _version_ | 1797052388458102784 |
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| author | Davies, S Loveridge, T Fatima, M Teixeira, C Clough, J |
| author_facet | Davies, S Loveridge, T Fatima, M Teixeira, C Clough, J |
| author_sort | Davies, S |
| collection | OXFORD |
| description | The synthesis of (SRSs[(phenylsulfinyl)benzene] chromium tricarbonyl 5 and (SRSs)-[(p-tolylsulfiny))benzene] chromium tricarbonyl 6 is achieved via a nucleophilic displacement reaction between the anion derived from (benzene) chromium tricarbonyl 9 and a suitable sulfinate ester. Replacing the sulfinate ester with a chiral sulfinyl-transfer reagent allows the isolation of the non-racemic sulfinyl-substituted complexes with good enantioselectivities (ee 80-89%) under optimised conditions. The use of Kagan's cyclic sulfite methodology for the synthesis of an enantiomerically pure tert-butylsulfinyl complex is unsuccessful, but results in the identification of a novel fragmentation - isomerisation process of the intermediate sulfinate. © The Royal Society of Chemistry 1999. |
| first_indexed | 2024-03-06T18:30:55Z |
| format | Journal article |
| id | oxford-uuid:09a2a2ce-9abe-4015-a101-dd9833f322a2 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T18:30:55Z |
| publishDate | 1999 |
| record_format | dspace |
| spelling | oxford-uuid:09a2a2ce-9abe-4015-a101-dd9833f322a22022-03-26T09:19:20ZAsymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:09a2a2ce-9abe-4015-a101-dd9833f322a2EnglishSymplectic Elements at Oxford1999Davies, SLoveridge, TFatima, MTeixeira, CClough, JThe synthesis of (SRSs[(phenylsulfinyl)benzene] chromium tricarbonyl 5 and (SRSs)-[(p-tolylsulfiny))benzene] chromium tricarbonyl 6 is achieved via a nucleophilic displacement reaction between the anion derived from (benzene) chromium tricarbonyl 9 and a suitable sulfinate ester. Replacing the sulfinate ester with a chiral sulfinyl-transfer reagent allows the isolation of the non-racemic sulfinyl-substituted complexes with good enantioselectivities (ee 80-89%) under optimised conditions. The use of Kagan's cyclic sulfite methodology for the synthesis of an enantiomerically pure tert-butylsulfinyl complex is unsuccessful, but results in the identification of a novel fragmentation - isomerisation process of the intermediate sulfinate. © The Royal Society of Chemistry 1999. |
| spellingShingle | Davies, S Loveridge, T Fatima, M Teixeira, C Clough, J Asymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexes |
| title | Asymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexes |
| title_full | Asymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexes |
| title_fullStr | Asymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexes |
| title_full_unstemmed | Asymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexes |
| title_short | Asymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexes |
| title_sort | asymmetric synthesis of sulfinyl substituted arene chromium tricarbonyl complexes |
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