97024-55-0Relevant articles and documents
Electrochemical [4+2] Annulation-Rearrangement-Aromatization of Styrenes: Synthesis of Naphthalene Derivatives
Ma, Yueyue,Lv, Jufeng,Liu, Chengyu,Yao, Xiantong,Yan, Guoming,Yu, Wei,Ye, Jinxing
supporting information, p. 6756 - 6760 (2019/04/17)
We report the first electrochemical strategy to synthesize functionalized naphthalene derivatives through [4+2] annulation—rearrangement–aromatization from styrenes under mild conditions. The electrolysis does not require metals, oxidants and high valence substrates, indicating the atom and step-economy ideals. The dehydrodimer produced through [4+2] cycloaddition of 4-methoxy α-methyl styrene is isolated and proved to be the key intermediate for the following oxydehydrogenation to form carbon cation, which undergoes rearrangement–aromatization to afford the final products. This reaction represents a powerful access to construct multi-substituted naphthalene blocks in a single step.
Electrophilic Bromolactonization of Cyclopropyl Carboxylic Acids Using Lewis Basic Sulfide Catalyst
Ke, Zhihai,Wong, Ying-Chieh,See, Jie Yang,Yeung, Ying-Yeung
supporting information, p. 1719 - 1724 (2016/06/09)
A highly facile and efficient electrophilic bromolactonization of cyclopropylcarboxylic acids could be effected by a Lewis basic sulfide catalyst. Mechanistic studies performed revealed that the cyclopropane substrates could undergo radical bromination upon exposure to light, yielding a mixture of regioisomers. In stark contrast, the Lewis basic sulfide catalyst could promote the electrophilic bromolactonization and yield the Markovnikov product exclusively.
Asymmetric bromolactonization using amino-thiocarbamate catalyst
Zhou, Ling,Tan, Chong Kiat,Jiang, Xiaojian,Chen, Feng,Yeung, Ying-Yeung
supporting information; experimental part, p. 15474 - 15476 (2011/02/21)
A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of γ-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.