1291082-19-3Relevant academic research and scientific papers
Weak arene C-h×××o hydrogen bonding in palladium-catalyzed arylation and vinylation of lactones
Huang, Zhiyan,Chen, Zuliang,Lim, Li Hui,Quang, Gia Chuong Phan,Hirao, Hajime,Zhou, Jianrong
supporting information, p. 5807 - 5812 (2013/07/05)
Weak force in action: In the title reaction, the palladium catalyst (see figure, left) uses weak CH×××O hydrogen bonding to control the absolute configuration of the new stereocenter. A similar palladium catalyst (right) used conventional NH×××O hydrogen bonding to guide stereoselection. Copyright
Regioselective hydroformylation of allylic alcohols
Lightburn, Thomas E.,De Paolis, Omar A.,Cheng, Ka H.,Tan, Kian L.
, p. 2686 - 2689 (2011/06/28)
A highly regioselective hydroformylation of allylic alcohols is reported toward the synthesis of β-hydroxy-acid and aldehyde products. The selectivity is achieved through the use of a ligand that reversibly binds to alcohols in situ, allowing for a directed hydroformylation to occur. The application to trisubstituted olefins was also demonstrated, which yields a single diastereomer product consistent with a stereospecific addition of CO and hydrogen.
Steering reaction pathways: From benzyl Claisen rearrangements to powerful ionic shifts
Valerio, Viviana,Madelaine, Claire,Maulide, Nuno
supporting information; experimental part, p. 4742 - 4745 (2011/05/19)
Take a walk on the wild side: A novel benzyl Claisen cascade rearrangement of keteniminium salts is described. The reaction leads to α-arylated lactones under metal-free conditions (top scheme; Tf=trifluoromethanesulfonyl). It is further demonstrated that the cationic intermediates involved can be steered away from pericyclic reaction manifolds into powerful ionic shifts through reaction design (bottom scheme). Copyright
