1322669-90-8Relevant academic research and scientific papers
Generation of Donor/Donor Copper Carbenes through Copper-Catalyzed Diyne Cyclization: Enantioselective and Divergent Synthesis of Chiral Polycyclic Pyrroles
Hong, Feng-Lin,Wang, Ze-Shu,Wei, Dong-Dong,Zhai, Tong-Yi,Deng, Guo-Cheng,Lu, Xin,Liu, Rai-Shung,Ye, Long-Wu
, p. 16961 - 16970 (2019)
The generation of metal carbenes from readily available alkynes represents a significant advance in metal carbene chemistry. However, most of these transformations are based on the use of noble-metal catalysts and successful examples of such an asymmetric version are still very scarce. Here a copper-catalyzed enantioselective cascade cyclization of N-propargyl ynamides is reported, enabling the practical and atom-economical construction of diverse chiral polycyclic pyrroles in generally good to excellent yields with wide substrate scope and excellent enantioselectivities (up to 97:3 e.r.). Importantly, this protocol represents the first copper-catalyzed asymmetric diyne cyclization. Moreover, mechanistic studies revealed that the generation of donor/donor copper carbenes is presumably involved in this 1,5-diyne cyclization, which is distinctively different from the related gold catalysis, and thus it constitutes a novel way for the generation of donor/donor metal carbenes.
Indium(III)-Catalyzed Cyclization of Aromatic 5-Enynamides: Facile Synthesis of 2-Aminonaphthalenes, 2-Amino-1H-indenes, and 2,3-Dihydro-1H-indeno[2,1-b]pyridines
Yeh, Ming-Chang P.,Liang, Chia-Jung,Chen, Hsiao-Feng,Weng, Yu-Ting
supporting information, p. 3242 - 3254 (2015/11/03)
Indium(III)-catalyzed cyclization reactions of aromatic 5-enynamides were studied. Indium triflate enabled the efficient synthesis of 2-aminonaphthalenes and 2-amino-1H-indenes from aromatic N-methyl-N-tosyl-ynamides bearing an ortho-vinyl and -isobutenyl group, respectively. The aromatic N-3-arylpropargylynamides bearing an ortho-gem-dihalovinyl subunit underwent a tandem cyclization/carbobromination reaction in the presence of indium tribromide to provide the dibrominated 2,3-dihydro-1H-indeno[2,1-b]pyridine derivatives in good yields.
Gold-catalyzed oxidative cyclization of 1,5-enynes using external oxidants
Vasu, Dhananjayan,Hung, Hsiao-Hua,Bhunia, Sabyasachi,Gawade, Sagar Ashok,Das, Arindam,Liu, Rai-Shung
supporting information; experimental part, p. 6911 - 6914 (2011/09/12)
Golden circle: Two gold-catalyzed oxidative cyclizations of 1,5-enynes using 8-methylquinoline N-oxide are presented (see example). Experimental results indicate that both reactions proceed through prior oxidation of alkyne to form α-carbonyl intermediate
