Research

 

Research Publication
Asst Visiting Prof of Chemistry Robert Iafe
10/8/2013
 
 
Robert Iafe, Visiting Assistant Professor of Chemistry in Keck Science, is first author on a communication published in Organic Letters. The article, “Increasing the Efficiency of the Transannular Diels–Alder Strategy via Palladium(II)-Catalyzed Macrocyclizations” was written together with Jonathan Kuo, Dustin Hochstatter, Tomomi Saga, Jonathan Turner, and Craig Merlic in the Department of Chemistry and Biochemistry at UCLA. In this research, the development and application of palladium(II)-catalyzed macrocyclizations as an approach to prepare transannular Diels–Alder (TADA) substrates was reported. α,ω-Diynes were selectively hydroborated to bis(boronate esters), which cyclize under palladium(II) catalysis producing TADA reaction substrates. The macrocycle is preorganized such that cycloaddition at room temperature can occur concomitantly with cyclization. Various functional groups were tolerated including esters, ethers, and sulfonamides. The cyclization strategy was demonstrated to be a strategically efficient approach to TADA substrates by a direct head-to-head comparison with a specific target previously prepared by a palladium(0)-catalyzed Stille strategy.  
http://pubs.acs.org/doi/abs/10.1021/ol303394t  

 

Back to News List