52263-41-9Relevant academic research and scientific papers
Catalytic, Regioselective Hydrocarbofunctionalization of Unactivated Alkenes with Diverse C-H Nucleophiles
Yang, Kin S.,Gurak, John A.,Liu, Zhen,Engle, Keary M.
supporting information, p. 14705 - 14712 (2016/11/18)
Reactions that forge carbon-carbon (C-C) bonds are the bedrock of organic synthesis, widely used across the chemical sciences. We report a transformation that enables C-C bonds to be constructed from two classes of commonly available starting materials, alkenes and carbon-hydrogen (C-H) bonds. The reaction employs a palladium(II) catalyst and utilizes a removable directing group to both control the regioselectivity of carbopalladation and enable subsequent protodepalladation. A wide range of alkenes and C-H nucleophiles, including 1,3-dicarbonyls, aryl carbonyls, and electron-rich aromatics, are viable reaction partners, allowing Michael-type reactivity to be expanded beyond α,β-unsaturated carbonyl compounds to unactivated alkenes. Applications of this transformation in drug diversification and natural product total synthesis are described. Stoichiometric studies support each of the proposed steps in the catalytic cycle.
Catalytic enantioselective conjugate addition of Grignard reagents to cyclic α,β-unsaturated carbonyl compounds
Kanai, Motomu,Nakagawa, Yuichi,Tomioka, Kiyoshi
, p. 3843 - 3854 (2007/10/03)
A catalytic asymmetric conjugate addition reaction of organocopper reagents, generated from copper salt, a chiral phosphine, and Grignard reagent, with cyclohexenone is highly dependent on the counter anion of copper species, solvents, Grignard reagents,
