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Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation
Hélène Guyon1, Anne Boussonnière1, Anne-Sophie Castanet1
1Université du Maine and CNRS UMR 6283, Institut des Molécules et Matériaux du Mans , Faculté des Sciences et Techniques, avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France.
The Journal of Organic Chemistry
|April 11, 2017
Abstract:
A new class of chiral 1,2-amino ether ligands, readily accessible from naturally occurring α-amino- or α-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 enantioselectivity.