Highly diastereoselective preparation of chiral NHC-boranes stereogenic at the boron atom
| Autor: | Béatrice Tuccio, Jean-Luc Parrain, Carlotta Figliola, Olivier Chuzel, Gaëlle Chouraqui, Paola Nava, Amel Abdou Mohamed, Clara Aupic |
|---|---|
| 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), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR-16-CE07-0002,BORON-HAT-TRICK,L'élément bore : une pierre angulaire pour la catalyse avec les espèces borénium, boryles et diborènes(2016) |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Radical-nucleophilic aromatic substitution
Bicyclic molecule 010405 organic chemistry Chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Enantioselective synthesis chemistry.chemical_element Boranes General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences 3. Good health Stereocenter Main group element Stereoselectivity Boron |
| Zdroj: | Chemical Science Chemical Science, 2019, 10 (26), pp.6524-6530. ⟨10.1039/C9SC01454C⟩ Chemical Science, The Royal Society of Chemistry, 2019, 10 (26), pp.6524-6530. ⟨10.1039/C9SC01454C⟩ |
| ISSN: | 2041-6520 2041-6539 |
| Popis: | Stereogenic main group elements, a promising strategy for metal-free enantioselective catalysis. Stereogenic main group elements are clearly generating interest in the enantioselective catalysis field. Surprisingly, while chiral organoboron reagents are very useful in stereoselective transformations, few scaffolds stereogenic at boron and configurationally stable have been reported to date. Herein, we describe an original library of chiral NHC-boranes, stereogenic at the boron atom, that has been prepared in only a few steps and in good yields (up to 93%). Key steps involve a chlorination/arylation sequence in the presence of simple Grignard reagents from bicyclic NHC-boranes. The high and unprecedented diastereoselectivity observed during the second step (up to 99 : 1 dr) has been rationalized through a plausible SRN1 mechanism thanks to EPR observations and DFT calculations. |
| Databáze: | OpenAIRE |
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