Enantioselective
Cycloaddition of Styrenes with Aldimines
Catalyzed by a Chiral Magnesium Potassium Binaphthyldisulfonate Cluster
as a Chiral Brønsted Acid Catalyst
Version 2 2017-06-19, 17:58
Version 1 2017-06-19, 17:54
Posted on 2017-06-19 - 17:58
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 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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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. Collection. https://doi.org/10.1021/jacs.7b04795
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AUTHORS (3)
MH
Manabu Hatano
KN
Keisuke Nishikawa
KI
Kazuaki Ishihara
KEYWORDS
Mechanistic aspectsAldimines CatalyzedChiral Br ønstedUseful transformationsEnantioselective CycloadditionChiral Magnesium Potassium Binaphthyldisulfonate Clustercatalyst precursorschiral Br ønsted acid catalystESI-MS analysisgram scalekinetics studyBr ønsted acidityenantioselective cycloadditionchiral magnesium potassium binaphthyldisulfonate cluster