New Way to Make Amide Bonds

Jeffrey Johnston and co-workers at Vanderbilt University have published in Nature on a new way to make amide bonds by reacting a bromo-nitro compound and an amine group in the presence of NIS.

Nature paper

Making Enones

The benzoin condensation takes advantage of umpolung chemistry where the aldehyde, which is normally an electrophile, is used as a nucleophile.  Frank Glorius and co-workers from Organisch-Chemisches Institut der Westfalischen Wilhelms-Universitat Munster have made use of this umpolung reactivity and used an alkyne as the reactant with the aldehyde.

JACS paper

Umpolung Reaction

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.

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

Cascade Metathesis

Paul Hanson at the University of Kansas came out with a nice paper on cascade metathesis reactions.

Tetrahedron paper

Salinosporamide A

Jeff Bode’s group at UPenn has come up with a new way to make salinosporamide using his carbene reaction. The intramolecular NHC reaction is a nice way to make the lactam framework of the molecule. You can check the paper out in Tetrahedron.

Tetrahedron paper

Carbene Catalysis

Jeffrey Bode at University of Pennsylvania has come up with a JACS paper that is based on his carbene methodology to make new carbon carbon bonds.

JACS link