Umpolung Reactivity of in Situ Generated Phosphido-Boranes: An Entry to P-Stereogenic Aminophosphine-Boranes
| Autor: | Romain Membrat, Didier Nuel, Sébastien Lemouzy, Damien Hérault, Enzo Olivieri, Laurent Giordano, Gérard Buono, Marion Jean, Muriel Albalat |
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| Přispěvatelé: | Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2019 |
| Předmět: |
In situ
Substitution reaction 010405 organic chemistry Chemistry Stereochemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry education Boranes 010402 general chemistry 01 natural sciences 0104 chemical sciences Stereocenter Umpolung Nucleophile [CHIM]Chemical Sciences Reactivity (chemistry) Protecting group |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2019, pp.4551-4557. ⟨10.1021/acs.joc.9b00333⟩ Journal of Organic Chemistry, American Chemical Society, 2019, ⟨10.1021/acs.joc.9b00333⟩ Journal of Organic Chemistry, 2019, 84, pp.4551-4557. ⟨10.1021/acs.joc.9b00333⟩ |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | International audience; The synthesis of P-stereogenic aminophos-phine-boranes has been developed on the basis of umpolung reactivity of in situ generated alkylarylphosphido-boranes, which are normally configurationally unstable intermediates. In our case, their high configurational stability was due to the slow release of the hydroxyalkyl protecting group, together with the fast formation of the iodophosphanylborane in the presence of N-iodosuccinimide. The subsequent substitution reaction was found to proceed in moderate to good yields and in a very high stereospecifity (es) using a variety of amines as nucleophiles. |
| Databáze: | OpenAIRE |
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