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.
Expansion of substrate scope for nitroxyl radical/copper-catalyzed aerobic oxidation of primary alcohols: A guideline for catalyst selection
Iwabuchi, Yoshiharu,Nagasawa, Shota,Sasaki, Ryota,Sasano, Yusuke,Yamaichi, Aoto
, p. 488 - 497 (2021/05/27)
Four distinctive sets of optimum nitroxyl radical/copper salt/additive catalyst combinations have been identified for accommodating the aerobic oxidation of various types of primary alcohols to their corresponding aldehydes. Interestingly, less nucleophilic catalysts exhibited higher catalytic activities for the oxidation of particular primary allylic and propargylic alcohols to give α,β-unsaturated aldehydes that function as competent Michael acceptors. The optimum conditions identified herein were successful in the oxidation of various types of primary alcohols, including unprotected amino alcohols and divalent-sulfur-containing alcohols in good-to-high yields. Moreover, N-protected alaninol, an inefficient substrate in the nitroxyl radical/ copper-catalyzed aerobic oxidation, was oxidized in good yield. On the basis of the optimization results, a guideline for catalyst selection has been established.
Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde
Chen, Xiaojuan,Fu, Liping,Huo, Xiaoli,Shao, Jiaan,Yu, Liya,Zeng, Linghui,Zhang, Chong,Zhang, Jiankang,Zhu, Huajian
supporting information, p. 16430 - 16433 (2021/10/01)
A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and good tolerance of various substituents make it an alternative approach to previous protocols, and potential applications of these investigated compounds are expected with or without post-modifications.
