Ether-directed, palladium(II)-catalyzed aza-Claisen rearrangements

ORGN 260

Andrew G. Jamieson, andjam@chem.gla.ac.uk, WestChem, Department of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, United Kingdom and Andrew Sutherland, Department of Chemistry, WESTCHEM, University of Glasgow, Glasgow, G12 8QQ, United Kingdom.
As part of a broad programme directed towards new metal mediated processes for natural product synthesis we have recently developed a highly stereoselective palladium(II) catalysed Overman rearrangement of allylic trichloroacetimidates which uses a chiral MOM-ether group to direct the facial coordination of the catalyst. Various preparative and mechanistic aspects of this process will be presented as well as current studies towards the preparation of natural products that have revealed the versatility and scope of this transformation.

 

Asymmetric Reactions and Syntheses
8:00 AM-11:40 AM, Monday, 11 September 2006 Moscone Center -- Room 131, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006