Catalytic nucleophilic ‘umpoled’ pi-allyl reagents
| Autor: | Renata Marcia de Figueiredo, Gilles Niel, Jean-Marc Campagne, Kim Spielmann |
|---|---|
| Přispěvatelé: | Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier ( ICGM ICMMM ), Université Montpellier 1 ( UM1 ) -Université Montpellier 2 - Sciences et Techniques ( UM2 ) -Ecole Nationale Supérieure de Chimie de Montpellier ( ENSCM ) -Université de Montpellier ( UM ) -Centre National de la Recherche Scientifique ( CNRS ) |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
electrophiles
diastereo- and regioselectivities outcome using nucleophilic p-allyl-metals chemistry.chemical_element Enantio 010402 general chemistry 01 natural sciences etc Catalysis Key properties of nucleophilic p-allyl-reagents: metals Transition metal Nucleophile [ CHIM.ORGA ] Chemical Sciences/Organic chemistry Reactivity (chemistry) Strategies to reverse the reactivity of p-allyl metals by changing the metal environment scope 010405 organic chemistry Chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Enantioselective synthesis General Chemistry Combinatorial chemistry 0104 chemical sciences Perspectives of this methodology: the use of alternative and greener precursors and conditions Reagent Applications of catalytic and asymmetric reactions in the total synthesis of natural products Electrophile Palladium |
| Zdroj: | Chemical Society Reviews Chemical Society Reviews, Royal Society of Chemistry, 2018, 47, pp.1159-1173. ⟨10.1039/c7cs00449d⟩ Chemical Society Reviews, Royal Society of Chemistry, 2018, 47, pp.1159-1173. 〈10.1039/c7cs00449d〉 |
| ISSN: | 0306-0012 1460-4744 |
| Popis: | International audience; After seminal Tsuji-Trost reactions (palladium catalyzed allylation of nucleophiles via -allyl intermediates as electrophiles),the idea of reversal reactivity of -allyl intermediates (i.e. -allyl as nucleophiles) has been stated since the eighties. Thanks to different transition metal sources and the modification of their electronic environment through the use of additives and ligands, such ‘reactivity switch’ of -allyl intermediates proved its powerfulness allowing high control in regio-, diastereo- and enantio-selectivities. These methodologies have thus emerged as efficient methods in the catalytic enantioselective allylation of carbonyl compounds and imines with a deep impact in natural product and/or drug elaboration. This tutorial review highlights the concept of ‘umpoled’ reactivity of -allyl intermediates, relying on selected recent examples. |
| Databáze: | OpenAIRE |
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