Removing triphenylphosphine oxide

I have had this silly problem in trying to get rid of triphenylphosphine oxide from my reaction mixture.  It’s stuck with my final product and can be a pain.  Some tricks I’ve seen are the use of dissolving mixture (O=PPh3 and product) in ether and run through short pad of silica.  This would be great if my product weren’t so polar – instead my product does not elute with ether.  Another trick was from this Lipshutz paper in 2003 where they used Merrifield resin to scavenge the phosphine.

 

OL paper

Schisanwilsonene A synthesis

Antonio Echavarran and co-workers at ICIQ have reported in ACIE on a synthesis of schisanwilsonene A.

ACIE paper

Hypervalent iodine promoted aryl shift

Thomas Wirth and co-workers at Cardiff University have reported in ACIE on a hypervalent iodine reagent promoted migration of an aryl group.

ACIE paper

Aspidophytine synthesis

Fayang Qiu and co-workers at Chinese Academy of Sciences have reported in ACIE on a synthesis of aspidophytine.

ACIE paper

DYKAT

Jeffrey Johnson and co-workers at UNC have reported in Org Lett on a dynamic kinetic resolution.

OL paper

Ni-catalyzed acyl cross-coupling

Sarah Reisman and co-workers have reported in JACS on a Ni-catalyzed coupling of an aryl chloride and acyl chloride.

JACS paper

[3,3]-Sigmatropic

Laszlo Kurti and co-workers from UT Southwestern have reported in JACS on a [3,3]-sigmatropic rearrangement approach to access BINAM derivatives using a phosphoric acid catalyst.

JACS paper

Rhizopodin synthesis

Ian Paterson and co-workers from the University of Cambridge have reported in ACIE on the synthesis of rhizopodin.

ACIE paper

Oxazoles to pyridines

Pierre Yves-Renard and co-workers from CNRS have reported in Organic Letters on an interesting synthesis of pyridines.

OL paper

Which point group is that organocatalyst?

Hiromichi Fujioka and co-workers from Osaka University have reported in Organic Letters on a kinetic resolution of a  bromo-carboxylic acid using a C3-symmetric organocatalyst.

OL paper