Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation
| Autor: | Hélène Guyon, Anne-Sophie Castanet, Anne Boussonnière |
|---|---|
| Přispěvatelé: | Institut des Molécules et Matériaux du Mans (IMMM), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
010405 organic chemistry
Chemistry Stereochemistry Ligand [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Chiral ligand Enantioselective synthesis ACHIRAL OLEFINIC ORGANOLITHIUMS Ether BETA-UNSATURATED ALDIMINE 010402 general chemistry 01 natural sciences CYCLIZATION 0104 chemical sciences ALPHA-AMINO-ACIDS ALPHA chemistry.chemical_compound TERTIARY DIAMINES Intramolecular force BROMINE-LITHIUM EXCHANGE HYDROXY CARBOXYLIC-ACIDS CONJUGATE ADDITION ASYMMETRIC-SYNTHESIS CHIRAL LIGAND |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2017, 82 (9), pp.4949-4957. ⟨10.1021/acs.joc.7b00423⟩ |
| ISSN: | 0022-3263 1520-6904 |
| Popis: | International audience; A new class of chiral 1,2-amino ether ligands, readily accessible from naturally occurring alpha-amino- or alpha-hydroxy acids, was found to provide high levels of both conversion and stereocontrol (up to 95:5 er) in intramolecular carbolithiation reactions, outperforming the benchmark ligand (-)-sparteine. The ligand could, be used in a substoichiometric amount (0.25 equiv) without significant loss of enantios electivity. |
| Databáze: | OpenAIRE |
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