196952-70-2Relevant academic research and scientific papers
Allenone-Mediated Racemization/Epimerization-Free Peptide Bond Formation and Its Application in Peptide Synthesis
Wang, Penghui,Wang, Xuewei,Wang, Zhengning,Zhao, Junfeng
supporting information, p. 10374 - 10381 (2021/07/26)
Allenone has been identified as a highly effective peptide coupling reagent for the first time. The peptide bond was formed with an α-carbonyl vinyl ester as the key intermediate, the formation and subsequent aminolysis of which proceed spontaneously in a racemization-/epimerization-free manner. The allenone coupling reagent not only is effective for the synthesis of simple amides and dipeptides but is also amenable to peptide fragment condensation and solid-phase peptide synthesis (SPPS). The robustness of the allenone-mediated peptide bond formation was showcased incisively by the synthesis of carfilzomib, which involved a rare racemization-/epimerization-free N to C peptide elongation strategy. Furthermore, the successful synthesis of the model difficult peptide ACP (65-74) on a solid support suggested that this method was compatible with SPPS. This method combines the advantages of conventional active esters and coupling reagents, while overcoming the disadvantages of both strategies. Thus, this allenone-mediated peptide bond formation strategy represents a disruptive innovation in peptide synthesis.
Revisiting the Addition of in-situ Nucleophiles to Allenic Ketones: An Entry Towards Synthesis of Benzodioxins
Sahoo, Sushree Ranjan,Sarkar, Debayan
supporting information, p. 1727 - 1731 (2020/03/13)
The manuscript delineates a revisit towards regioselective addition of in situ generated negative nucleophiles to allenic ketones in the presence of a base. A wide variety of allenic ketones as well as nucleophiles are viable in this transformation. A dir
Base-promoted direct synthesis of functionalized: N -arylindoles via the cascade reactions of allenic ketones with indoles
Li, Shengxiao,Wu, Xin-Xing,Chen, Shufeng
supporting information, p. 789 - 793 (2019/01/30)
A convenient Cs2CO3-promoted cascade benzannulation reaction of allenic ketones with indoles was achieved for the synthesis of functionalized N-arylindole derivatives under transition-metal-free conditions. A series of readily available starting materials can undergo the process successfully. It represents a practical method for the construction of N-arylindole scaffolds with high atom economy.
Cycloisomerization of Conjugated Allenones into Furans under Mild Conditions Catalyzed by Ligandless Au Nanoparticles
Zorba, Leandros,Kidonakis, Marios,Saridakis, Iakovos,Stratakis, Manolis
supporting information, p. 5552 - 5555 (2019/08/01)
Au nanoparticles supported on TiO2 (1 mol %) catalyze the quantitative cycloisomerization of conjugated allenones into furans under very mild conditions. The reaction rate is accelerated by adding acetic acid (1 equiv), but the acid does not participate in the protodeauration step as in the corresponding Au(III)-catalyzed transformation. The process is purely heterogeneous, allowing thus the recycling and reuse of the catalyst effectively in several runs.
Diverging Pathways in the Activation of Allenes with Lewis Acids and Bases: Addition, 1,2-Carboboration, and Cyclization
Melen, Rebecca L.,Wilkins, Lewis C.,Kariuki, Benson M.,Wadepohl, Hubert,Gade, Lutz H.,Hashmi, A. Stephen K.,Stephan, Douglas W.,Hansmann, Max M.
supporting information, p. 4127 - 4137 (2015/09/01)
The reactions of allenes with frustrated (or cooperative) Lewis acid/base pairs result in the 1,4-addition of the base pair to the allene. The reactions of allenyl ketones and esters just in the presence of the strong Lewis acid B(C6F5/su
Synthesis of Acyl Alkenylindium Reagents and Their Application in the Synthesis of (Z)-α,β-Unsaturated Ketones via Palladium-Catalyzed Cross-Coupling Reaction
Park, Youngchul,Min, Jiae,Eom, Dahan,Lee, Phil Ho
supporting information, p. 3934 - 3937 (2015/08/19)
A synthetic method for the preparation of acyl alkenylindium reagents was developed involving the hydroindation reaction of allenyl ketones with indium and indium chloride in methanol under mild conditions. Their synthetic applications were demonstrated from Pd-catalyzed cross-coupling reactions with aryl bromides and iodides and alkenyl and aryl triflates for the synthesis of (Z)-α,β-unsaturated ketones.
Gold-catalyzed regioselective synthesis of 2- and 3-alkynyl furans
Li, Yifan,Brand, Jonathan P.,Waser, Jerome
supporting information, p. 6743 - 6747 (2013/07/26)
Chemical Matching: C2- or C3-alkynylated furans were selectively synthesized by using gold catalysis. Direct C-H alkynylation of furans was achieved with C2 selectivity, and a domino cyclization/alkynylation process starting from allenes gave C3-alkynylat
Room temperature Fe(NO3)3·9H 2O/TEMPO/NaCl-catalyzed aerobic oxidation of homopropargylic alcohols
Liu, Jinxian,Ma, Shengming
, p. 10161 - 10167 (2013/11/06)
A practical and eco-friendly aerobic oxidation of homopropargylic alcohols using Fe(NO3)3·9H2O/TEMPO/NaCl as catalysts at room temperature under atmospheric pressure was developed affording corresponding homopropargylic ke
Tandem reactions of 1,2-allenic ketones leading to substituted benzenes and α,β-unsaturated nitriles
Zhang, Xinying,Jia, Xuefei,Fang, Liangliang,Liu, Nan,Wang, Jianji,Fan, Xuesen
supporting information; experimental part, p. 5024 - 5027 (2011/11/12)
One-pot double Michael addition/intramolecular aldol reaction/ decarboxylation of 1,2-allenic ketones with cyanoacetate offers an efficient and convenient approach to highly functionalized benzenes. With 2-substituted cyanoacetates, the reaction proceeds via a different tandem process to afford α,β-unsaturated nitriles effectively.
A halide-initiated aza-Baylis-Hillman reaction: Generation of unnatural amino acids
Davis, Lindsey O.,Tobey, Suzanne L.
supporting information; experimental part, p. 6078 - 6081 (2011/01/04)
A series of allenic ketones react with a glyoxylate-derived imine in the presence of MgBr2 through an aza-Morita-Baylis-Hillman (MBH) reaction. The isolation of a variety of unnatural amino acids with unique allene-containing functional groups
