130788-41-9Relevant 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.
Palladium-Catalyzed α-Arylation of Vinylogous Esters for the Synthesis of γ,γ-Disubstituted Cyclohexenones
Johnson, Thomas,Pultar, Felix,Menke, Friedericke,Lautens, Mark
, p. 6488 - 6491 (2016/12/23)
A palladium-catalyzed α-arylation of cyclic vinylogous esters to form products that are converted in one step to γ-alkyl-γ-aryl-substituted cyclohexenones is reported. This Pd-catalyzed reaction proceeds at room temperature, is generally high-yielding, and uses an amount of a commercially available catalyst as low as 0.25 mol %. The scope of aryl bromides is particularly broad, and alkenyl bromides can also be used. This two-step protocol, comprising α-arylation and reductive transposition, can be performed in one pot and is applicable to gram-scale synthesis.
Chiral synthesis of 6,7-benzomorphans: Synthesis of ( -)1(S),2(S),4(R),6(R)-1,2,3,4,5,6-hexahydro-2,6-methano-8-methoxy -1,3,4,6-tetramethyl-3-benzazocine through the chromium hexacarbonyl mediated cyclisation of 1(S),1 ′(R)-1,2-dihydro-7-methoxy-1,4-dimethyl -1 (N-methy-N-trifluoroacetamido-1′-methylethan-2′-yl)naphthalene
Sainsbury, Malcolm,Mahon, Mary F.,Williams, Colin S.,Naylor, Alan,Scopes, David I. C.
, p. 4195 - 4210 (2007/10/02)
(-)1(S),2(S),4(R),6(R)-1,2,3,4,5,6-Hexahydro-2,6-methano-8-methoxy- 1,3,4,6-tetramethyl-3-benzazocine has been synthesised in 86 % enandomeric excess from the α-(v6-chromium tricarbonyl) complex of 1 (S), 1′(R)-1,2-dihydro-7-methoxy-1,4-dimethyl-1-(N-methyl-N-trifluoroacetamido- 1′-methylethan-2/-yl)naphthalene. A precursor of this compound is 2(R),4(,S)-4-(3-methoxyphenyl)-2,4-dimethylcyclohexanone which was obtained through an Enders' type C-methylation reaction of 4-(3-methoxyphenyl)4-methylcyclohexanone using SAMP as the reagent.
