23431-56-3Relevant articles and documents
Enantioselective Assembly of Cycloenones with a Nitrile-Containing All-Carbon Quaternary Center from Malononitriles Enabled by Ni Catalysis
Lu, Zhiwu,Hu, Xu-Dong,Zhang, Hui,Zhang, Xiao-Wen,Cai, Jinhui,Usman, Muhammad,Cong, Hengjiang,Liu, Wen-Bo
, p. 7328 - 7333 (2020/08/19)
Chiral nitriles are valuable molecules in modern organic synthesis and drug discovery. Selectively differentiating the two nitrile groups of widely available malononitrile derivatives is a straightforward yet underdeveloped route to construct enantioenriched nitriles. Here we report an enantioselective nickel-catalyzed desymmetrization of malononitriles for the generation of nitrile-containing all-carbon quaternary stereocenters. This protocol involves a nickel-catalyzed addition of aryl boronic acids to alkynes, followed by a selective nitrile insertion, providing unprecedented access to enantioenriched 5-7-membered α-cyano-cycloenones with a fully substituted olefin from a broad range of substrates. The synthetic utility of these nitrile products is demonstrated by gram-scale synthesis and conversion to several useful functional groups.
Rhodium-Catalyzed asymmetric synthesis of spirocarbocycles: arylboron reagents as surrogates of 1,2-dimetalloarenes
Shintani, Ryo,Isobe, Shingo,Takeda, Momotaro,Hayashi, Tamio
supporting information; experimental part, p. 3795 - 3798 (2010/08/20)
(Figure Presented) Revolutionary Rh-oad: A rhodium/dienecatalyzed addition of sodium tetraarylborates to alkyne-tethered 2-cydoalken-lones has been developed for the synthesis of splrocarbocycles. The tetraarylborates catalytlcally form two new carbon-carbon bonds. A chlral diene ligand also asymmetrically creates quaternary spirocarbon stereocenters with high enantiomeric purity.
