Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation

Hélène Guyon (1) , Anne Boussonniere (1) , Anne-Sophie Castanet (1)

1 IMMM - Institut des Molécules et Matériaux du Mans

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.

Mots clés: BROMINE-LITHIUM EXCHANGE; ACHIRAL OLEFINIC ORGANOLITHIUMS; HYDROXY CARBOXYLIC-ACIDS; ALPHA-AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; CHIRAL LIGAND; ALPHA; BETA-UNSATURATED ALDIMINE; TERTIARY DIAMINES; CYCLIZATION

Domaines: Chimie organique

Hélène Guyon, Anne Boussonniere, Anne-Sophie Castanet. Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation. Journal of Organic Chemistry, 2017, 82 (9), pp.4949-4957. ⟨10.1021/acs.joc.7b00423⟩. ⟨hal-02163261⟩