7534-40-9Relevant articles and documents
The Allylic Acetoxylation of 1,1-Disubstituted Alkenes Catalyzed by a Palladium(II)/Monothiadiazole Ligand System
Jin, Can,Li, Xiaohan,Sun, Bin,Wang, Jiayang,Yang, Jin,Yu, Chuangming,Zhang, Xun,Zhuang, Xiaohui
supporting information, p. 1479 - 1483 (2019/07/15)
A palladium(II)/monothiadiazole ligand catalytic system and its application in catalyzing the acetoxylation of 1,1-disubstituted alkenes have been developed. With this newly designed monothiadiazole thioether ligand, the reaction showed a broad scope with respect to 1,1-disubstituted olefins, giving the corresponding products in yields of 30-86percent.
Palladium-Catalyzed Asymmetric Allylic Alkylation of 4-Substituted Isoxazolidin-5-ones: Straightforward Access to β2,2-Amino Acids
Nascimento de Oliveira, Marllon,Arseniyadis, Stellios,Cossy, Janine
supporting information, p. 4810 - 4814 (2018/03/21)
We report here an unprecedented and highly enantioselective palladium-catalyzed allylic alkylation applied to 4-substituted isoxazolidin-5-ones. Ultimately, the process provides a straightforward access to β2,2-amino acids bearing an all-carbon quaternary stereogenic center in great yields and a high degree of enantioselectivity.
Stereoselective Synthesis of a Highly Oxygenated δ-Lactone Related to the Core Structure of (-)-Enterocin
Wegmann, Marcus,Bach, Thorsten
supporting information, p. 209 - 217 (2016/12/24)
The title compound was prepared in a concise route starting from an appropriately protected (S)-glyceraldehyde. A highly diastereoselective (d.r. >95:5) Mukaiyama aldol reaction of an acetoacetate-derived silyl enol ether served as the initial step of the synthetic sequence. It was found that protection of the glyceraldehyde as a butane-2,3-dione acetal is required to achieve the desired diastereoselectivity. Upon lactonization, a Tsuji-Trost allylation and a subsequent one-pot reaction cascade including an ozonolysis and an α-hydroxylation gave diastereoselective access to the desired α-hydroxy-β-oxo-δ-lactone. Alternative synthetic approaches are discussed and proof for the configuration of the product is presented.
