Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles
The first enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles, enabled by a bifunctional iminophosphorane (BIMP) organocatalyst, is described. The iminophosphorane moiety of the catalyst provides the required basicity to deprotonate the thiol nucleophile while the chira...
| Main Authors: | , , , , , |
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| Format: | Journal article |
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Royal Society of Chemistry
2018
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| _version_ | 1797052945587503104 |
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| author | Formica, M Sorin, G Farley, A Díaz, J Paton, R Dixon, D |
| author_facet | Formica, M Sorin, G Farley, A Díaz, J Paton, R Dixon, D |
| author_sort | Formica, M |
| collection | OXFORD |
| description | The first enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles, enabled by a bifunctional iminophosphorane (BIMP) organocatalyst, is described. The iminophosphorane moiety of the catalyst provides the required basicity to deprotonate the thiol nucleophile while the chiral scaffold and H-bond donor control facial selectivity. The reaction is broad in scope with respect to the thiol and benzimidazole reaction partners with the reaction proceeding in up to 98% yield and 96:4 er. |
| first_indexed | 2024-03-06T18:37:39Z |
| format | Journal article |
| id | oxford-uuid:0bcff2af-b6fc-4fd6-b6be-14c10c3f0a6c |
| institution | University of Oxford |
| last_indexed | 2024-03-06T18:37:39Z |
| publishDate | 2018 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:0bcff2af-b6fc-4fd6-b6be-14c10c3f0a6c2022-03-26T09:31:25ZBifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazolesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:0bcff2af-b6fc-4fd6-b6be-14c10c3f0a6cSymplectic Elements at OxfordRoyal Society of Chemistry2018Formica, MSorin, GFarley, ADíaz, JPaton, RDixon, DThe first enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles, enabled by a bifunctional iminophosphorane (BIMP) organocatalyst, is described. The iminophosphorane moiety of the catalyst provides the required basicity to deprotonate the thiol nucleophile while the chiral scaffold and H-bond donor control facial selectivity. The reaction is broad in scope with respect to the thiol and benzimidazole reaction partners with the reaction proceeding in up to 98% yield and 96:4 er. |
| spellingShingle | Formica, M Sorin, G Farley, A Díaz, J Paton, R Dixon, D Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles |
| title | Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles |
| title_full | Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles |
| title_fullStr | Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles |
| title_full_unstemmed | Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles |
| title_short | Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles |
| title_sort | bifunctional iminophosphorane catalysed enantioselective sulfa michael addition of alkyl thiols to alkenyl benzimidazoles |
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