138371-79-6Relevant academic research and scientific papers
Nickel-Catalyzed Desymmetric Hydrogenation of Cyclohexadienones: An Efficient Approach to All-Carbon Quaternary Stereocenters
You, Cai,Li, Xiuxiu,Gong, Quan,Wen, Jialin,Zhang, Xumu
, p. 14560 - 14564 (2019/10/11)
Nickel-catalyzed desymmetric hydrogenation has been achieved. With the Ni(OTf)2/(S,S)-Ph-BPE system, a series of ?,?-disubstituted cyclohexadienones were transformed to the corresponding cyclohexenones with a chiral all-carbon quaternary center at the γposition in high yields (92-98%) and excellent enantioselectivities (92%-99% ee). This catalytic system can also tolerate the desymmetric reaction of spirocarbocyclic cyclohexadienones to produce the corresponding cyclohexenones bearing a chiral spiro quaternary carbon with high yields (94%-98%) and ee values (96%-99% ee). Furthermore, this methodology provides an efficient and concise synthetic route to the intermediate of natural products cannabispirenones A and B.
Asymmetric Synthesis of Remote Quaternary Centers by Copper-Catalyzed Desymmetrization: An Enantioselective Total Synthesis of (+)-Mesembrine
Bokka, Apparao,Mao, James X.,Hartung, John,Martinez, Steven R.,Simanis, Justin A.,Nam, Kwangho,Jeon, Junha,Shen, Xiaoqiang
, p. 5158 - 5162 (2018/09/13)
Catalytic asymmetric syntheses of remote quaternary stereocenters have been developed by copper-catalyzed 1,4-hydrosilylation of ?,?-disubstituted cyclohexadienones. A variety of cyclohexenones have been synthesized in good yield and excellent enantioselectivity. Versatile 2-silyloxy diene intermediates bearing ?,?-disubstituted all carbon stereogenic centers can be isolated from the mild reaction conditions. The utility of this strategy is exemplified in a catalytic asymmetric total synthesis of (+)-mesembrine.
Novel synthesis of 2-aryl or 4-arylcyclohexenones
Berrier, C.,Gaillard, E.,Jacquesy, J. C.,Jouannetaud, M. P.,Kigabo, F.
, p. 537 - 543 (2007/10/02)
In anhydrous HF, 4-hydroxy-4-methylcyclohex-2-en-1-one 5 reacts with aromatics (benzene, toluene, anisole, para-bromoanisole) to yield 2 and 4 arylated ketones.Reaction with benzene yields enone 2 (73percent).With toluene, reaction affords enone 6 (24perc
