Enantioselective Cycloaddition of Styrenes with Aldimines Catalyzed by a Chiral Magnesium Potassium Binaphthyldisulfonate Cluster as a Chiral Brønsted Acid Catalyst

Published on 2017-06-19T17:58:47Z (GMT) by
A chiral magnesium potassium binaphthyldisulfonate cluster, as a chiral Brønsted acid catalyst, was shown to catalyze an enantioselective cycloaddition of styrenes with aldimines for the first time. The strong Brønsted acidity of the catalyst precursors, which might dissolve drying agents and take up the leached Mg<sup>2+</sup> and K<sup>+</sup>, serendipitously led to good enantioselectivity. Mechanistic aspects were supported by X-ray and ESI-MS analysis of the catalyst and a kinetics study of the reaction. Useful transformations to optically active 1,3-amino alcohols on a gram scale were also demonstrated.

Cite this collection

Hatano, Manabu; Nishikawa, Keisuke; Ishihara, Kazuaki (2017): Enantioselective

Cycloaddition of Styrenes with Aldimines

Catalyzed by a Chiral Magnesium Potassium Binaphthyldisulfonate Cluster

as a Chiral Brønsted Acid Catalyst. ACS Publications.

https://doi.org/10.1021/jacs.7b04795

Retrieved: 20:53, Jun 26, 2017 (GMT)