Syntheses of homochiral 1,2-ferrocene-functionalized Lewis acids and acid/base pairs
We report a facile approach for the synthesis of homochiral 1,2-disubstituted ferrocene-functionalized Lewis acids and acid/base pairs. The synthesis is based on chiral induction facilitated by the ortho sulfinyl subsitutent in S-Fc{S(O)p-tol}, S-1, to obtain the key intermediate S,S p-1,2-fc{S(O)p-...
| Main Authors: | , , |
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| Format: | Journal article |
| Language: | English |
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2011
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| _version_ | 1797067980160368640 |
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| author | Siewert, I Vidovic, D Aldridge, S |
| author_facet | Siewert, I Vidovic, D Aldridge, S |
| author_sort | Siewert, I |
| collection | OXFORD |
| description | We report a facile approach for the synthesis of homochiral 1,2-disubstituted ferrocene-functionalized Lewis acids and acid/base pairs. The synthesis is based on chiral induction facilitated by the ortho sulfinyl subsitutent in S-Fc{S(O)p-tol}, S-1, to obtain the key intermediate S,S p-1,2-fc{S(O)p-tol}(BMes2), S,Sp-2a (p-tol = C6H4Me-4, Mes = C6H2Me 3-2,4,6). Subsequent substitution of the -S(O)p-tol substituent in S,Sp-2a gives access to a range of enantiomerically pure S p-1,2-ferrocene-functionalized Lewis acids and acid/base pairs including the first homochiral 1-phosphino-2-borylferrocene. Enantiomeric excesses (e.e.s) of >95% have typically been achieved using this methodology. © 2011 Elsevier B.V. All rights reserved. |
| first_indexed | 2024-03-06T22:04:06Z |
| format | Journal article |
| id | oxford-uuid:4f939be1-bcf0-4029-8fd5-3a231cac00bc |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T22:04:06Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | oxford-uuid:4f939be1-bcf0-4029-8fd5-3a231cac00bc2022-03-26T16:08:02ZSyntheses of homochiral 1,2-ferrocene-functionalized Lewis acids and acid/base pairsJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:4f939be1-bcf0-4029-8fd5-3a231cac00bcEnglishSymplectic Elements at Oxford2011Siewert, IVidovic, DAldridge, SWe report a facile approach for the synthesis of homochiral 1,2-disubstituted ferrocene-functionalized Lewis acids and acid/base pairs. The synthesis is based on chiral induction facilitated by the ortho sulfinyl subsitutent in S-Fc{S(O)p-tol}, S-1, to obtain the key intermediate S,S p-1,2-fc{S(O)p-tol}(BMes2), S,Sp-2a (p-tol = C6H4Me-4, Mes = C6H2Me 3-2,4,6). Subsequent substitution of the -S(O)p-tol substituent in S,Sp-2a gives access to a range of enantiomerically pure S p-1,2-ferrocene-functionalized Lewis acids and acid/base pairs including the first homochiral 1-phosphino-2-borylferrocene. Enantiomeric excesses (e.e.s) of >95% have typically been achieved using this methodology. © 2011 Elsevier B.V. All rights reserved. |
| spellingShingle | Siewert, I Vidovic, D Aldridge, S Syntheses of homochiral 1,2-ferrocene-functionalized Lewis acids and acid/base pairs |
| title | Syntheses of homochiral 1,2-ferrocene-functionalized Lewis acids and acid/base pairs |
| title_full | Syntheses of homochiral 1,2-ferrocene-functionalized Lewis acids and acid/base pairs |
| title_fullStr | Syntheses of homochiral 1,2-ferrocene-functionalized Lewis acids and acid/base pairs |
| title_full_unstemmed | Syntheses of homochiral 1,2-ferrocene-functionalized Lewis acids and acid/base pairs |
| title_short | Syntheses of homochiral 1,2-ferrocene-functionalized Lewis acids and acid/base pairs |
| title_sort | syntheses of homochiral 1 2 ferrocene functionalized lewis acids and acid base pairs |
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