28469-52-5Relevant academic research and scientific papers
Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution
Liu, En-Chih,Topczewski, Joseph J.
supporting information, p. 5308 - 5313 (2021/05/04)
The triazole heterocycle has been widely adopted as an isostere for the amide bond. Many native amides are α-chiral, being derived from amino acids. This makes α-N-chiral triazoles attractive building blocks. This report describes the first enantioselective triazole synthesis that proceeds via nickel-catalyzed alkyne-azide cycloaddition (NiAAC). This dynamic kinetic resolution is enabled by a spontaneous [3,3]-sigmatropic rearrangement of the allylic azide. The 1,4,5-trisubstituted triazole products, derived from internal alkynes, are complementary to those commonly obtained by the related CuAAC reaction. Initial mechanistic experiments indicate that the NiAAC reaction proceeds through a monometallic Ni complex, which is distinct from the CuAAC manifold.
Intramolecular Tandem Seleno-Michael/Aldol Reaction: A Simple Route to Hydroxy Cyclo-1-ene-1-carboxylate Esters
Banachowicz, Piotr,Mlynarski, Jacek,Buda, Szymon
, p. 11269 - 11277 (2018/09/06)
Intramolecular tandem seleno-Michael/aldol reaction followed by an oxidation-elimination process can be an efficient tool for the construction of hydroxy cyclo-1-ene-1-carboxylate esters from oxo-α,β-unsaturated esters. Generation of lithium selenolate from elemental selenium and n-BuLi provides a simple and efficient one-pot access to cyclic endo-Morita-Baylis-Hillman adducts.
CYCLIC COMPOUNDS
-
Paragraph 0649; 0650; 0651, (2016/11/24)
The present invention provides compounds having a Toll-like receptor 4 (TLR4) signaling inhibitory action useful as preventive and therapeutic drugs of inflammatory disease and/or central nervous system disease or diseases such as chemotherapy-induced peripheral neuropathy (CIPN), chemotherapy-induced neuropathic pain (CINP), liver injury, ischemia-reperfusion injury (IRI) and the like. The present invention relates to a compound represented by formula (I) and a salt thereof: (wherein, each symbol is explained in greater detail in the specification).
Copper-catalyzed asymmetric allylic alkylation of racemic cyclic substrates: Application of dynamic kinetic asymmetric transformation (DYKAT)
Langlois, Jean-Baptiste,Alexakis, Alexandre
supporting information; experimental part, p. 447 - 457 (2010/06/13)
The copper-catalyzed asymmetric allylic alkylation (AAA) is of great interest in organic synthesis. This reaction was extensively studied using a broad range of substrates, ligands and organometallic reagents. However, the use of racemic substrates was still limited. Although some processes of kinetic resolution are reported in the literature, no examples of quantitative deracemization are described as is the case for the Pd-catalyzed allylic alkylation. We present here a full account of our investigations through the development of the first example of such a process in copper-catalyzed AAA. High enantioselectivities (up to 99% ee), scope of the reaction and mechanistic considerations are reported herein.
Assessing the scope of the tandem Michael/intramolecular aldol reaction mediated by secondary amines, thiols and phosphines
Richards, Elinor L,Murphy, Patrick J,Dinon, Francesca,Fratucello, Silvia,Brown, Paul M,Gelbrich, Thomas,Hursthouse, Michael B
, p. 7771 - 7784 (2007/10/03)
The outcome of a tandem Michael/intramolecular aldol reaction which is mediated by secondary amines, thiols and phosphines has been found to be highly substrate dependent, with the best results being obtained for the formation of 5 and 6-membered rings using thiol or thiolate nucleophiles. Amine and phosphine mediated cyclisations were found to be problematic in several cases but were still effective methods for the formation of 5-7 membered rings.
Stereo controlled synthesis of 1β-aminoalkylcarbapenems and tricyclic carbapenems (trinems)
Iso, Yasuyoshi,Nishitani, Yasuhiro
, p. 2287 - 2308 (2007/10/03)
The effective synthesis of 1β-aminoalkylcarbapenems and trinems are described and the antibacterial activities of new carbapenem derivatives prepared by this advantageous synthetic method are also reported.
Optically active 2-alkoxy-carbonyl-2-cycloalkene derivatives and a process for producing the derivatives
-
, (2008/06/13)
The present invention relates to optically active 2-alkoxycarbonyl-2-cycloalkene derivatives, especially optically active 2-alkoxycarbonyl-2-cycloalkene-1-ols, useful as starting materials of pharmaceuticals, agricultural chemicals and the like, and optic
Enantiocomplementary Synthesis of Functionalized Cycloalkenol Building Blocks Using Lipase
Takano, Seiichi,Yamane, Takahiro,Takahashi, Michiyasu,Ogasawara, Kunio
, p. 837 - 840 (2007/10/02)
Racemic 2-carbethoxy-2-cyclopenten-1-ol and racemic 2-carbethoxy-2-cyclohexen-1-ol afforded the corresponding (R)-acetates leaving the corresponding (S)-alcohols unchanged upon treatment with v
LA REACTION DE WITTIG-HORNER EN MILIEU HETEROGENE IX. BIS ALDOLISATION DES PHOSPHONATES A PARTIR DES DIALDEHYDES ALIPHATIQUES EN MILIEU AQUEUX PEU BASIQUE. SYNTHESE DE CYCLENOLS FONCTIONNELS.
Graff, M.,Dilaimi, A. Al,Seguineau, P.,Rambaud, M.,Villieras, J.
, p. 1577 - 1578 (2007/10/02)
Aqueous solutions of glutaraldehyde and succinaldehyde give respectively improved yields of 1-functional 6-cyclohexenols and 5-cyclopentenols, when subjected to WITTIG-HORNER reaction in water at room temperature, with potassium carbonate as a base.
