1334209-70-9Relevant academic research and scientific papers
Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration
Shu, Xing-Zhong,Li, Xiaoxun,Shu, Dongxu,Huang, Suyu,Schienebeck, Casi M.,Zhou, Xin,Robichaux, Patrick J.,Tang, Weiping
, p. 5211 - 5221 (2012/05/05)
A new type of rhodium-catalyzed [5 + 2] cycloaddition was developed for the synthesis of seven-membered rings with diverse functionalities. The ring formation was accompanied by a 1,2-acyloxy migration event. The five- and two-carbon components of the cycloaddition are 3-acyloxy-1,4-enynes (ACEs) and alkynes, respectively. Cationic rhodium(I) catalysts worked most efficiently for the intramolecular cycloaddition, while only neutral rhodium(I) complexes could facilitate the intermolecular reaction. In both cases, electron-poor phosphite or phosphine ligands often improved the efficiency of the cycloadditions. The scope of ACEs and alkynes was investigated in both the intra- and intermolecular reactions. The resulting seven-membered-ring products have three double bonds that could be selectively functionalized.
Interception of a rautenstrauch intermediate by alkynes for [5+2] cycloaddition: Rhodium-catalyzed cycloisomerization of 3-acyloxy-4-ene-1,9- diynes to bicyclo[5.3.0]decatrienes
Shu, Xing-Zhong,Huang, Suyu,Shu, Dongxu,Guzei, Ilia A.,Tang, Weiping
, p. 8153 - 8156 (2011/10/03)
Rholling in the bicycles: A rhodium(I)-catalyzed cycloisomerization for the synthesis of bicyclic compounds containing a cycloheptatriene ring from linear alkenynes (see scheme; cod=1,5-cyclooctadiene) is proposed to proceed through 1,2-acyloxy migration, 6 π electrocyclization, migratory insertion, and reductive elimination. The overall process can be viewed as a novel intramolecular [5+2] cycloaddition with concomitant 1,2-acyloxy migration.
