Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: application to the ketimine nitro-Mannich reaction.
The design, synthesis, and development of a new class of modular, strongly basic, and tunable bifunctional Brønsted base/H-bond-donor organocatalysts are reported. These catalysts incorporate a triaryliminophosphorane as the Brønsted basic moiety and are readily synthesized via a last step Staudinge...
| Autori principali: | , , |
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| Natura: | Journal article |
| Lingua: | English |
| Pubblicazione: |
2013
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| _version_ | 1826275015458291712 |
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| author | Núñez, MG Farley, A Dixon, D |
| author_facet | Núñez, MG Farley, A Dixon, D |
| author_sort | Núñez, MG |
| collection | OXFORD |
| description | The design, synthesis, and development of a new class of modular, strongly basic, and tunable bifunctional Brønsted base/H-bond-donor organocatalysts are reported. These catalysts incorporate a triaryliminophosphorane as the Brønsted basic moiety and are readily synthesized via a last step Staudinger reaction of a chiral organoazide and a triarylphosphine. Their application to the first general enantioselective organocatalytic nitro-Mannich reaction of nitromethane to unactivated ketone-derived imines allows the enantioselective construction of β-nitroamines possessing a fully substituted carbon atom. The reaction is amenable to multigram scale-up, and the products are useful for the synthesis of enantiopure 1,2-diamine and α-amino acid derivatives. |
| first_indexed | 2024-03-06T22:52:16Z |
| format | Journal article |
| id | oxford-uuid:5f31585d-bce2-401b-9c64-a7ece952fcf1 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T22:52:16Z |
| publishDate | 2013 |
| record_format | dspace |
| spelling | oxford-uuid:5f31585d-bce2-401b-9c64-a7ece952fcf12022-03-26T17:45:21ZBifunctional iminophosphorane organocatalysts for enantioselective synthesis: application to the ketimine nitro-Mannich reaction.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:5f31585d-bce2-401b-9c64-a7ece952fcf1EnglishSymplectic Elements at Oxford2013Núñez, MGFarley, ADixon, DThe design, synthesis, and development of a new class of modular, strongly basic, and tunable bifunctional Brønsted base/H-bond-donor organocatalysts are reported. These catalysts incorporate a triaryliminophosphorane as the Brønsted basic moiety and are readily synthesized via a last step Staudinger reaction of a chiral organoazide and a triarylphosphine. Their application to the first general enantioselective organocatalytic nitro-Mannich reaction of nitromethane to unactivated ketone-derived imines allows the enantioselective construction of β-nitroamines possessing a fully substituted carbon atom. The reaction is amenable to multigram scale-up, and the products are useful for the synthesis of enantiopure 1,2-diamine and α-amino acid derivatives. |
| spellingShingle | Núñez, MG Farley, A Dixon, D Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: application to the ketimine nitro-Mannich reaction. |
| title | Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: application to the ketimine nitro-Mannich reaction. |
| title_full | Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: application to the ketimine nitro-Mannich reaction. |
| title_fullStr | Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: application to the ketimine nitro-Mannich reaction. |
| title_full_unstemmed | Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: application to the ketimine nitro-Mannich reaction. |
| title_short | Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: application to the ketimine nitro-Mannich reaction. |
| title_sort | bifunctional iminophosphorane organocatalysts for enantioselective synthesis application to the ketimine nitro mannich reaction |
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