4197-79-9Relevant academic research and scientific papers
Catalytic asymmetric [2+2] cycloaddition between quinones and fulvenes and a subsequent stereoselective isomerization to 2,3-dihydrobenzofurans
Zheng, Haifeng,Xu, Chaoran,Wang, Yan,Kang, Tengfei,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
supporting information, p. 6585 - 6588 (2017/07/10)
The catalytic enantioselective [2+2] cycloaddition between quinones and fulvenes was achieved, for the first time, by the use of a chiral copper(ii) complex catalyst. The transformation afforded a series of enantiomerically enriched [6,4,5]-tricyclic cyclobutane derivatives in good yields with excellent regio- and stereoselectivities. Furthermore, the [2+2] adducts could be easily converted into formal [3+2] adducts efficiently and stereoselectively.
Chiral cobalt(II) complex catalyzed Friedel-Crafts aromatization for the synthesis of axially chiral biaryldiols
Xu, Chaoran,Zheng, Haifeng,Hu, Bowen,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
supporting information, p. 9741 - 9744 (2017/09/07)
An efficient atroposelective synthesis of axially chiral biaryldiols via asymmetric Friedel-Crafts aromatization between p-quinones and 2-naphthols was developed. A chiral cobalt(ii) complex of N,N′-dioxide enabled the process to generate axially chiral biaryldiols in up to 98% yield and 95% ee. A large range of substituents at different positions of p-quinones and 2-naphthols was tolerable. The configuration of the product and the chiral N,N′-dioxide-Co(ClO4)2 catalyst was identified by X-ray crystal diffraction analysis and a possible catalytic model was suggested.
Substituent effects in the oxidation of 2-alkyl-1,4-dialkoxybenzenes with ceric ammonium nitrate
Love, Brian E.,Simmons, Alexander L.
, p. 5712 - 5715 (2016/11/29)
Increased steric size of alkyl groups and the presence of coordinating atoms on alkoxy groups have both been found to contribute to decreasing yields of diquinones upon reaction of 2-alkyl-1,4-dialkoxybenzenes with CAN. The overall hydrophilicity of the substrates does not appear to be a significant factor in determining the diquinone yield for these reactions.
Effects of reaction conditions on quinone/diquinone product ratios in the oxidation of 1,4-dimethoxybenzene derivatives with ceric ammonium nitrate
Love, Brian E.,Duffy, Brian C.,Simmons, Alexander L.
supporting information, p. 1994 - 1997 (2014/04/03)
Proper choice of reaction conditions allows formation of either the quinone or corresponding diquinone as the major product upon treatment of 2-alkyl-1,4-dimethoxybenzenes with ceric ammonium nitrate.
