Asymmetric copper-catalyzed Diels-Alder reaction revisited: control of the structure of bis(oxazoline) ligands

Paul Le Maux (1) , Vincent Dorcet (1) , Gérard Simonneaux (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

Synthesis of 1,4-bis(oxazoline) ligands bearing a bicyclo[2,2,2]backbone derived from 9,10-dihydro-9,10-ethanoanthacene trans-dicarboxylic acid was revisited. Starting from L- or D-amino alcohols and either (S,S) or (R,R)-dihydroethano trans-dicarboxylic acid, a complete series of ligands was evaluated in the copper-catalyzed Diels-Alder reaction. The most efficient ligands with a phenyl substituent on the oxazoline ring afforded enantiomeric excess up to 98%. This is different from previous results indicating that the best enantioselectivity involved a diastereomeric ligand with the meso-backbone.

Mots clés: Chiral bis(oxazoline) synthesis; Bicyclo[2.2.2] backbone; Diels-Alder catalysis; Copper; Enantioselectivity

Domaines: Autre

Paul Le Maux, Vincent Dorcet, Gérard Simonneaux. Asymmetric copper-catalyzed Diels-Alder reaction revisited: control of the structure of bis(oxazoline) ligands. Tetrahedron, 2013, 69 (38), pp.8291-8298. ⟨10.1016/j.tet.2013.06.093⟩. ⟨hal-00840883⟩