56893-15-3Relevant academic research and scientific papers
Catalytic Cyclooligomerization of Enones with Three Methylene Equivalents
Farley, Conner M.,Zhou, You-Yun,Banka, Nishit,Uyeda, Christopher
supporting information, p. 12710 - 12714 (2018/10/09)
Cyclic structures are highly represented in organic molecules, motivating a wealth of catalytic methods targeting their synthesis. Among the various ring-forming processes, cyclooligomerization reactions possess several attractive features but require addressing a unique challenge associated with controlling ring-size selectivity. Here we describe the catalytic reductive cocyclooligomerization of an enone and three carbene equivalents to generate a cyclopentane, a process that constitutes a formal [2 + 1 + 1 + 1]-cycloaddition. The reaction is promoted by a (quinox)Ni catalyst and uses CH2Cl2/Zn as the C1 component. Mechanistic studies are consistent with a metallacycle-based pathway, featuring sequential migratory insertions of multiple carbene equivalents to yield cycloalkanes larger than cyclopropanes.
Design and synthesis of 3-trifluoromethyl-3h-pyrazoles and further investigations of their transformation to 1h-pyrazoles
Sha, Qiang,Liu, Haixuan,Wei, Yunyang
supporting information, p. 7707 - 7715 (2015/04/22)
An efficient intramolecular cycloaddition strategy for the synthesis of trifluoromethyl-substituted 3H-pyrazoles was developed. Subsequently, their wide applications were demonstrated: they (1) react with dioxane by a radical process and (2) undergo [1,5] sigmatropic rearrangements. These applications are useful as the products were obtained in high yields and with excellent regioselectivity.
Highly efficient route to functionalized tetrahydrocarbazoles using a tandem cross-metathesis/intramolecular-hydroarylation sequence
An, Xiao-Lei,Chen, Jia-Rong,Li, Chang-Feng,Zhang, Fu-Gen,Zou, You-Quan,Guo, Ying-Cen,Xiao, Wen-Jing
supporting information; experimental part, p. 2258 - 2265 (2011/06/11)
The scope of the novel ruthenium-catalyzed tandem cross-metathesis/ intramolecular-hydroarylation sequence is described. This methodology offers a practical and efficient synthesis of structurally diverse and complex tetrahydrocarbazoles in good to excellent yields (up to 98%). Moreover, preliminary efforts towards the development of an enantioselective version of the current process by sequential catalysis with ruthenium complex and chiral amine are presented, with high yields and enantioselectivities (up to 88% yield and 91% ee).
