Naturalproductman’s Blog

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Umpolung Reaction

Posted by naturalproductman on June 15, 2009

Talk about some new umpulong chemistry – John Verkade at Iowa State University has recently published in Tetrahedron Letters on a reaction that coupled a 1,3-dithiane moiety to an electrophile, which was in this case, an aldehyde.  The 1,3-dithiane was equipped with a TMS group in the 2 position and the catalyst that was used was a phosphino-amino-catalyst or a proazaphosphatrane catalyst. It’s a good complement to the N-heterocyclic carbene reactions that people such as Bode and Rovis like to use.

umpolung

TL paper

There is a recent JOC paper from the same authors that changed the starting material to an alpha-TMS-nitrile and can add to the scope of this reaction:

JOC link

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