Naturalproductman’s Blog

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Chiral Bronstead Acid Cyclization Cascade

Posted by naturalproductman on July 17, 2009

Darren Dixon and co-workers at the University of Oxford has recently published in JACS on a cascade intermolecular coupling between an enol lactone and tryptamine in the presence of R-BINOL phosphoric acid.  Basically it was a condensation between an amine with the enol lactone followed by an intramolecular Friedel Crafts.  This reaction had modest to great ee’s (72-99% ee) and is worth checking out.

bronstead acid

JACS paper


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