Naturalproductman’s Blog

Hey, is that a natural product?!

Nitrone-Ketene Coupling

Posted by naturalproductman on July 31, 2009

Andrew Smith and co-workers at the University of St. Andrews in the UK have recently published in Organic Letters where they have reported on a reaction cascade that involves a nucleophilic addition of the nitrone onto the ketene followed by a 3,3-sigmatropic rearrangement to eventually form an oxindole.  The reaction takes place in a dry ice bath temperature and the ketene is formed in-situ from an acid chloride with triethylamine.
ketene nitrone

OL paper

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: