160350-20-9Relevant academic research and scientific papers
Copper-Catalyzed Cope-Type Hydroamination of Nonactivated Olefins toward Cyclic Nitrones: Scope, Mechanism, and Enantioselective Process Development
Zhang, Mengru,Liu, Shuang,Li, Hexin,Guo, Yajing,Li, Na,Guan, Meihui,Mehfooz, Haroon,Zhao, Jinbo,Zhang, Qian
, p. 12620 - 12627 (2019/09/16)
The catalytic synthesis of cyclic nitrones, an important type of functional molecules for both synthetic chemistry and related fields, remains underdeveloped. Herein we report the copper-catalyzed Cope-type hydroamination of oximes with pendant nonactivated olefins, which enables facile access to a series of five- and six-membered cyclic nitrones under mild conditions. In this study, heterocycle-tethered oximes were employed in the Cope-type hydroamination reaction for the first time. High enantioselectivity was achieved for carbon-tethered γ,δ-vinyl oximes to afford enantioenriched five-membered cyclic nitrones. The results of preliminary mechanistic studies indicate a mononuclear catalytic species and a unified catalytic pathway over a large temperature range.
Enantioselective C-H bond functionalization triggered by radical trifluoromethylation of unactivated alkene
Yu, Peng,Lin, Jin-Shun,Li, Lei,Zheng, Sheng-Cai,Xiong, Ya-Ping,Zhao, Li-Jiao,Tan, Bin,Liu, Xin-Yuan
supporting information, p. 11890 - 11894 (2015/02/05)
An asymmetric unactivated alkene/C-H bond difunctionalization reaction for the concomitant construction of C-CF3 and C-Obonds was realized by using a Cu/Bronsted acid cooperative catalytic system, thus providing facile access to valuable chiral
Novel macrocyclic amidinoureas: Potent non-azole antifungals active against wild-type and resistant Candida species
Sanguinetti, Maurizio,Sanfilippo, Stefania,Castagnolo, Daniele,Sanglard, Dominique,Posteraro, Brunella,Donzellini, Giovanni,Botta, Maurizio
supporting information, p. 852 - 857 (2013/10/01)
Novel macrocyclic amidinourea derivatives 11, 18, and 25 were synthesized and evaluated as antifungal agents against wild-type and fluconazole resistant Candida species. Macrocyclic compounds 11 and 18 were synthesized through a convergent approach using as a key step a ring-closing metathesis macrocyclization reaction, whereas compounds 25 were obtained by our previously reported synthetic pathway. All the macrocyclic amidinoureas showed antifungal activity toward different Candida species higher or comparable to fluconazole and resulted highly active against fluconazole resistant Candida strains showing in many cases minimum inhibitory concentration values lower than voriconazole.
Sequential N-acylamide methylenation-enamide ring-closing metathesis: Construction of benzo-fused nitrogen heterocycles
Bennasar, M. Lluisa,Roca, Tomas,Monerris, Manuel,Garcia-Diaz, Davinia
, p. 7028 - 7034 (2007/10/03)
The dimethyltitanocene methylenation of N-acylamides derived from ortho-vinylanilines, ortho-allylaniline, and ortho-vinylbenzylamine provides the corresponding enamides, which upon exposure to the second generation Grubbs ruthenium catalyst give access to indoles, 1,4-dihydroquinolines, and 1,2-dihydroisoquinolines, respectively. This sequential protocol also allows the synthesis of dihydrobenzoazepines, although the ring-closing metathesis (RCM) step is complicated by the alkene isomerization processes. From certain substrates, the direct annulation is observed in the titanium-mediated step, which is likely to occur through an olefin metathesis-intramolecular olefination sequence.
