13019-08-4Relevant articles and documents
Reusable rhodium catalyst for the selective transvinylation of sp2-C linked carboxylic acid
Jiang, Ruihang,Chen, Zhangpei,Zhan, Kun,Liu, Lei,Zhou, Junjie,Ai, Yongjian,Li, Shuang,Bao, Hongjie,Hu, Ze'nan,Qi, Li,Wang, Jingting,Sun, Hong-bin
, p. 3279 - 3282 (2018/07/21)
The vinyl benzoate derivatives were successfully synthesized by the transvinylation reactions that vinyl group transferred from vinyl acetate to aromatic carboxylic acids with the recoverable catalyst RhCl3·3H2O. This catalyst features air stable and tolerance of water, good reusable ability, meanwhile, shows high selectivity for aromatic carboxylic acid in the presence of phenolic hydroxyl. With this method, a variety of vinyl benzoate derivatives can be produced with up to 95% yield.
Asymmetric Synthesis of Protected Cyclohexenylamines and Cyclohexenols by Rhodium-Catalyzed [2+2+2] Cycloaddition
Masutomi, Koji,Sugiyama, Haruki,Uekusa, Hidehiro,Shibata, Yu,Tanaka, Ken
supporting information, p. 15373 - 15376 (2016/12/03)
It has been established that cationic rhodium(I)/axially chiral biaryl bis(phosphine) complexes catalyze the asymmetric [2+2+2] cycloaddition of 1,6-enynes with electron-rich functionalized alkenes, enamides, and vinyl carboxylates, to produce the corresponding protected cyclohexenylamines and cyclohexenols. Interestingly, regioselectivity depends on structures of substrates. The present cycloaddition was successfully applied to the enantioselective total synthesis of (?)-porosadienone by using the amide moiety as a leaving group.
Ethenolate transfer reactions: A facile synthesis of vinyl esters
Appaye, Srinivasan Kaliyaperumal,Nikumbh, Satish Pandurang,Govindapur, Rajeshwar Reddy,Banerjee, Shyamapada,Bhalerao, Dinesh S.,Kumar, Unniaran K. Syam
, p. 1115 - 1122 (2014/09/17)
A simple and efficient metal-free ethenolate transfer reaction has been elaborated in moderate-to-high yields from vinyl acetate. This reaction was accomplished by generation of potassium ethenolate, which was then reacted with homo and mixed anhydrides of aliphatic, aryl and heteroaryl acids, to yield the corresponding vinyl esters. The utility of thus generated vinyl esters was then probed by carrying out intramolecular Heck reactions to give isobenzofuran-1(3H)-one derivatives in excellent yields. Copyright
Dinuclear zinc-catalyzed asymmetric desymmetrization of acyclic 2-substituted-1,3-propanediols: A powerful entry into chiral building blocks
Trost, Barry M.,Malhotra, Sushant,Mino, Takashi,Rajapaksa, Naomi S.
supporting information; experimental part, p. 7648 - 7657 (2009/08/19)
The asymmetric acylation of meso-2-substituted-1,3-propanediols by using an amphoteric chiral dinuclear zinc catalyst is described. It is has been demonstrated that both 2-alkyl- and 2-aryl-1,3-propanediols can be desymmetrized in high yields and enantioselectivities by using the same family of ligands. Given that both antipodes of the chiral catalyst are available, both enantiomers of the desymmetrized product can be obtained from the same starting material. The synthetic utility of the desymmetrized products has been demonstrated by the synthesis of several chiral building blocks with high enantiomeric purities.
