2579-22-8Relevant articles and documents
P-Stereogenic Phosphines Directed Copper(I)-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions
Gan, Zhenjie,Zhi, Mengna,Han, Ruiping,Li, Er-Qing,Duan, Zheng,Mathey, Fran?ois
, p. 2782 - 2785 (2019)
A new pair of P-stereogenic ligands with multiple chiral centers were synthesized and used in the copper(I)-catalyzed enatioselective [3 + 2] cycloaddition of iminoesters with alkenes. A variety of highly functionalized pyrrolidines were obtained in excellent yield and enatioselectivity. This is the first example of a pair of P-stereogenic ligands working as pseudoenantiomers to tune the enantio- and diastereoselective 1,3-dipolar cycloaddition, and providing a pair of enantiomerically pure pyrrolidines, respectively.
Copper-catalyzed TEMPO addition to propargyl alcohols for the synthesis of vinylic alkoxyamines
Kang, Ye-Won,Choi, Yoon-Jeong,Jang, Hye-Young
, p. 4842 - 4845 (2014)
A variety of vinylic alkoxyamines derived from propargyl alcohols and 2, 2, 6,6-tetramethylpiperidine N-oxyl (TEMPO) were synthesized in good yields under copper-catalyzed aerobic conditions. A reaction mechanism was proposed, involving the isomerization of propargyl radicals to allenic radicals, and related mechanistic studies were performed. The kinetic isotope effect on the propargyl C-H bond cleavage (α-deprotonation) reaction was observed (kH/kD = 3.76).
Highly efficient and mild synthesis of variously 5-substituted-4-carbaldehyde-1,2,3-triazole derivatives
Journet, Michel,Cai, Dongwei,Kowal, Jason J.,Larsen, Robert D.
, p. 9117 - 9118 (2001)
Synthesis of variously 5-substituted-4-carbaldehyde-1,2,3-triazole derivatives 2 was accomplished by reacting sodium azide with α,β-acetylenic aldehydes 1 in DMSO at room temperature. Therefore, the reaction remains basic avoiding the generation of the hazardous explosive HN3, resulting in a safe process. This mild and general reaction was instantaneous and was essentially quantitative.
Synthesis of 1,3-dioxacyclan-2-yl-substituted 1,2,3-triazoles
Zlotskii,Raskil’dina,Golovanov,Bormotin,Bekin
, p. 3 - 6 (2017)
A new method for preparing 4-(1,3-dioxacyclan-2-yl)-5-phenyl-1,2,3-triazoles in 30–75% yields has been developed on the basis of azide–alkyne cycloaddition to 2-phenylethinyl-1,3-dioxacyclanes. It has been shown that the best results are achieved when the reaction is carried out at 150–155°C in DMSO.
Controlled reduction of activated primary and secondary amides into aldehydes with diisobutylaluminum hydride
Azeez, Sadaf,Kandasamy, Jeyakumar,Sabiah, Shahulhameed,Sureshbabu, Popuri
supporting information, p. 2048 - 2053 (2022/03/31)
A practical method is disclosed for the reduction of activated primary and secondary amides into aldehydes using diisobutylaluminum hydride (DIBAL-H) in toluene. A wide range of aryl and alkyl N-Boc, N,N-diBoc and N-tosyl amides were converted into the corresponding aldehydes in good to excellent yields. Reduction susceptible functional groups such as nitro, cyano, alkene and alkyne groups were found to be stable. Broad substrate scope, functional group compatibility and quick conversions are the salient features of this methodology.
Synthesis of Chiral Propargylamines, Chiral 1,2-Dihydronaphtho[2,1-b]furans and Naphtho[2,1-b]furans with C-Alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals and β-Naphthols
Man, Ningning,Li, Yuming,Jie, Jiyang,Li, Hongyun,Yang, Haijun,Zhao, Yufen,Fu, Hua
supporting information, p. 12884 - 12889 (2021/07/28)
Chiral phosphoric acid-catalyzed couplings of C-alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals with β-naphthols led to chiral propargylamines in moderate to high yields with high to excellent enantioselectivity, in which the reactions underwent sequential chiral phosphoric acid-catalyzed in situ formation of N-(tert-butoxycarbonyl)-imines (N-Boc-imines) from the aminals, and 1,2-addition of β-naphthols to the N-Boc-imines. Chiral 1,2-dihydronaphtho[2,1-b]furans and naphtho[2,1-b]furans were prepared with satisfactory results when 10 mol% AgOAc and 20 mol% 2,6-lutidine or 1.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were added to the resulting chiral propargylamines solution, respectively.
Visible Light-Induced Cascade Cyclization of 3-Aminoindazoles, Ynals, and Chalcogens: Access to Chalcogen-Containing Pyrimido[1,2- b]-indazoles
Zhou, Jinlei,Li, Wen,Zheng, Huitao,Pei, Yongyan,Liu, Xiang,Cao, Hua
, p. 2754 - 2759 (2021/04/12)
A direct cascade cyclization of 3-aminoindazoles, ynals, and accessible chalcogens facilitated by visible light has been developed. A series of fluoroactive selenium/tellurium-substituted pyrimido[1,2-b]-indazoles were easily accessed in moderate to good yields with a broad scope. Furthermore, we surveyed the spectral properties of selenide pyrimido[1,2-b]-indazoles prepared by this method.
