69626-39-7Relevant 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
, 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.
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.
Base-promoted direct synthesis of functionalized: N -arylindoles via the cascade reactions of allenic ketones with indoles
Li, Shengxiao,Wu, Xin-Xing,Chen, Shufeng
, 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.
Regio- and Stereoselective Nickel-Catalyzed Coupling of Boronic Acids with Allenoates
Liu, Yang,Daka, Mario,Bandini, Marco
, p. 3187 - 3196 (2018/08/17)
The Ni(II)-catalyzed cross-coupling of arylboronic acids with allenoates is documented. The high regio- and stereoselectivity of the process enables a wide range of β-aryl β,γ-unsaturated esters to be prepared in good to excellent yields (up to 95%) and high E / Z -selectivity. Additionally, [3+2]-cascade sequence was observed when 2-formylphenylboronic acid was employed.
Gold-catalyzed domino cyclization-alkynylation reactions with EBX reagents: New insights into the reaction mechanism
Ghari, Hossein,Li, Yifan,Roohzadeh, Roohollah,Caramenti, Paola,Waser, Jerome,Ariafard, Alireza
, p. 12257 - 12262 (2017/09/25)
Gold-catalyzed domino processes constitute a useful alternative to C-H functionalization for the synthesis of functionalized (hetero)arenes. Herein, we report computational studies on the gold-catalyzed cyclization alkynylation of keto-allenes with ethyny
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.
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.
, 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
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
Gold-catalyzed regioselective synthesis of 2- and 3-alkynyl furans
Li, Yifan,Brand, Jonathan P.,Waser, Jerome
, 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
Tandem reaction of 3-hydroxyhexa-4,5-allenic esters: A novel access to diversely substituted 2H-pyran-2-ones and indenes
Xu, Haiyun,Zhang, Xinying,He, Yan,Guo, Shenghai,Fan, Xuesen
supporting information; experimental part, p. 3121 - 3123 (2012/04/18)
A highly efficient synthesis of diversely substituted 2H-pyran-2-ones and indenes through Bronsted acid promoted tandem reaction of the readily obtainable 3-hydroxyhexa-4,5-allenic esters under extremely mild conditions has been developed. The Royal Society of Chemistry 2012.
