This paper reports the development of a switchable asymmetric catalyst based on supramolecular helices to control multiple stereogenic centers in a single molecular scaffold. The catalyst, built on hydrogen-bonded assemblies of a benzene-1,3,5-tricarboxamide (BTA) achiral phosphine ligand and a chiral BTA comonomer, is used in a copper-hydride catalyzed hydrosilylation and hydroamination cascade. The stereoisomer obtained is controlled by the helix handedness, which can be switched by altering the chiral BTA comonomer. This strategy enables the one-pot synthesis of all four stereoisomers of an amino alcohol with comparable selectivities, either concomitantly or sequentially by switching helix handedness between reaction steps.

Ran Chen, Ahmad Hammoud, Paméla Aoun, Mayte A. Martínez-Aguirre, Nicolas Vanthuyne, Régina Maruchenko, Patrick Brocorens, Laurent Bouteiller, Matthieu Raynal