4.8 Article

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

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 25, Pages 8424-8427

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b04795

Keywords

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Funding

  1. JSPS KAKENHI [JP26105723, JP17H03054, JP15H05810]
  2. Grants-in-Aid for Scientific Research [17H03054, 15H05810] Funding Source: KAKEN

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A chiral magnesium potassium binaphthyldisulfonate cluster, as a chiral Bronsted acid catalyst, was shown to catalyze an enantioselective cycloaddition of styrenes with aldimines for the first time. The strong Bronsted acidity of the catalyst precursors, which might dissolve drying agents and take up the leached Mg2+ and K+, 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.

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