129313-47-9Relevant academic research and scientific papers
Regiocontrolled Reductive Vinylation of Aliphatic 1,3-Dienes with Vinyl Triflates by Nickel Catalysis
Pang, Xiaobo,Zhao, Zhen-Zhen,Wei, Xiao-Xue,Qi, Liangliang,Xu, Guang-Li,Duan, Jicheng,Liu, Xue-Yuan,Shu, Xing-Zhong
supporting information, p. 4536 - 4542 (2021/04/07)
The regiocontrolled functionalization of 1,3-dienes has become a powerful tool for divergent synthesis, yet it remains a long-standing challenge for aliphatic substrates. Herein, we report a reductive approach for a branch-selective 1,2-hydrovinylation of aliphatic 1,3-dienes with R-X electrophiles, which represents a new selectivity pattern for diene functionalization. Simple butadiene, aromatic 1,3-dienes, and highly conjugated polyene were also tolerated. The combination of Ni(0) and the phosphine-nitrile ligand generally resulted in >20:1 regioselectivity with the retention of the geometry of the C3-C4 double bonds. This reaction proceeds with a broad substrate scope, and it allows for the conjugation of two biologically active units to form more complex polyene molecules, such as tetraene and pentaene as well as heptaene.
A Concise and Highly Enantioselective Total Synthesis of (+)-anti- and (-)-syn-Mefloquine Hydrochloride: Definitive Absolute Stereochemical Assignment of the Mefloquines
Rastelli, Ettore J.,Coltart, Don M.
supporting information, p. 14070 - 14074 (2016/01/25)
A concise asymmetric (>99:1 e.r.) total synthesis of (+)-anti- and (-)-syn-mefloquine hydrochloride from a common intermediate is described. The key asymmetric transformation is a Sharpless dihydroxylation of an olefin that is accessed in three steps from commercially available materials. The Sharpless-derived diol is converted into either a trans or cis epoxide, and these are subsequently converted into (+)-anti- and (-)-syn-mefloquine, respectively. The synthetic (+)-anti- and (-)-syn-mefloquine samples were derivatized with (S)-(+)-mandelic acid tert-butyldimethylsilyl ether, and a crystal structure of each derivative was obtained. These are the first X-ray structures for mefloquine derivatives that were obtained by coupling to a known chiral, nonracemic compound, and provide definitive confirmation of the absolute stereochemistry of (+)-anti- as well as (-)-syn-mefloquine.
A study on the chiral inversion of mandelic acid in humans
Yevglevskis, Maksims,Bowskill, Catherine R.,Chan, Chloe C. Y.,Heng, Justin H.-J.,Threadgill, Michael D.,Woodman, Timothy J.,Lloyd, Matthew D.
, p. 6737 - 6744 (2014/08/18)
Mandelic acid is a chiral metabolite of the industrial pollutant styrene and is used in chemical skin peels, as a urinary antiseptic and as a component of other medicines. In humans, S-mandelic acid undergoes rapid chiral inversion to R-mandelic acid by a
A general methodology for automated solid-phase synthesis of depsides and depsipeptides. Preparation of a valinomycin analogue
Kuisle, Oliver,Quinoa, Emilio,Riguera, Ricardo
, p. 8063 - 8075 (2007/10/03)
A general methodology is described that allows the solid-phase synthesis of depsides and depsipeptides from chiral α-hydroxy- and α-amino acids. The results of studies with different protecting groups for the α-hydroxy acids and coupling systems for depsi
