62551-73-9Relevant academic research and scientific papers
Non-Bonding 1,4-Sulphur-Oxygen Interaction Governs the Reactivity of α-Ketothioesters in Triphenylphosphine-Catalyzed Cyclization with Acetylenedicarboxylates
Bankura, Abhijit,Saha, Jayanta,Maity, Rajib,Das, Indrajit
supporting information, p. 1014 - 1021 (2020/12/31)
α-Ketothioesters undergo triphenylphosphine (PPh3)-catalyzed cyclization with acetylenedicarboxylate esters smoothly, in contrast to α-ketooxoesters which require more drastic conditions with the limited substrate scope. The reaction works well
Diversification of α-ketoamides: Via transamidation reactions with alkyl and benzyl amines at room temperature
Junaid, Qazi Mohammad,Kandasamy, Jeyakumar,Popuri, Sureshbabu,Sabiah, Shahulhameed,Singh, Shweta
supporting information, p. 7134 - 7140 (2021/08/30)
A wide range of N-tosyl α-ketoamides underwent transamidation with various alkyl amines in the absence of a catalyst, base, or additive. On the other hand, transamidation in N-Boc α-ketoamides was achieved in the presence of Cs2CO3. The reactions proceede
Novel synthesis of tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones via decarboxylative cyclization reaction of α-amino acids and α-ketoamides
Wu, Jia-shou,Jiang, Hua-jiang,Yang, Jian-guo,Jin, Zheng-neng,Chen, Ding-ben
supporting information, p. 546 - 551 (2017/01/16)
An efficient and practical method was developed for the synthesis of tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones based on the decarboxylative cyclization reaction of α-ketoamides and proline. In most cases, tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones were obtained with perfect diastereoselectivity to give trans-isomer in excellent yield.
N-Heterocyclic Carbene-Catalyzed Umpolung of Alkynyl 1,2-Diketones
Kong, Xiangwen,Zhang, Guoxiang,Yang, Shuang,Liu, Xiaozhi,Fang, Xinqiang
supporting information, p. 2729 - 2734 (2017/08/23)
The umpolung of alkynyl 1,2-diketones via N-heterocyclic carbene (NHC) catalysis was achieved for the first time, allowing the rapid access to a large variety of synthetically and pharmaceutically important α-pyrones under very mild conditions. A completely new NHC-catalyzed umpolung pattern involving an O-acylated allenolate as the key intermediate was proposed. Moreover, an unprecedented reaction pathway, featured by a series of group migrations and new bond formation, was postulated to demonstrate the formation of the products. (Figure presented.).
C?H Insertion as a Key Step to Spiro-Oxetanes, Scaffolds for Drug Discovery
Nicolle, Simon M.,Nortcliffe, Andrew,Bartrum, Hannah E.,Lewis, William,Hayes, Christopher J.,Moody, Christopher J.
supporting information, p. 13623 - 13627 (2017/09/13)
A new route to spiro-oxetanes, potential scaffolds for drug discovery, is described. The route is based on the selective 1,4-C?H insertion reactions of metallocarbenes, generated from simple carbonyl precursors in flow or batch mode, to give spiro-β-lacto
Alkyl halide-free heteroatom alkylation and epoxidation facilitated by a recyclable polymer-supported oxidant for the in-flow preparation of diazo compounds
Nicolle, Simon M.,Hayes, Christopher J.,Moody, Christopher J.
supporting information, p. 4576 - 4579 (2015/03/18)
Highly reactive metal carbenes, generated from simple ketones via diazo compounds, including diazoamides and -phosphonates, using a recyclable reagent inflow, are transient but versatile electrophiles for heteroatom alkylation reactions and for epoxide formation. The method produces no organic waste, with the only byproducts being water, KI and nitrogen, without the attendant hazards of isolation of intermediate diazo compounds.
Organocatalytic Enantioselective Michael Reaction of Malononitrile with β,β-Disubstituted Nitroalkenes
Chen, Shengwei,Lou, Qinxin,Ding, Yuyang,Zhang, Shasha,Hu, Wenhui,Zhao, Junling
supporting information, p. 2437 - 2441 (2015/08/18)
We have developed and optimized an enantioselective Michael reaction of malononitrile with β,β-disubstituted nitroalkenes. This reaction was catalyzed by a cinchona alkaloid derived thiourea catalyst, producing products of high yields (up to 98 %) and ste
Nucleophilic β-Carbon Activation of Propionic Acid as a 3-Carbon Synthon by Carbene Organocatalysis
Jin, Zhichao,Jiang, Ke,Fu, Zhenqian,Torres, Jaume,Zheng, Pengcheng,Yang, Song,Song, Bao-An,Chi, Yonggui Robin
supporting information, p. 9360 - 9363 (2015/06/30)
Direct β-carbon activation of propionic acid (C2H5CO2H) by carbene organocatalysis has been developed. This activation affords the smallest azolium homoenolate intermediate (without any substituent) as a 3-carbon nucleophi
Amino Acid Salt Catalyzed Asymmetric Synthesis of 1,2-Diols with A Quaternary Carbon Center
Wu, Quanquan,Liu, Shulei,Wang, Fangyuan,Li, Qingqing,Cheng, Kangli,Li, Juan,Jiang, Jun
supporting information, p. 2442 - 2446 (2015/10/19)
Enantioenriched 1,2-diols with a quaternary carbon center have great potential in the preparation of natural and biologically active compounds, but remain challenging synthetic targets which demand for both good diastereo- and enantioselectivity. As part
Cationic Ir/Me-BIPAM-catalyzed asymmetric intramolecular direct hydroarylation of α-ketoamides
Shirai, Tomohiko,Ito, Hajime,Yamamoto, Yasunori
supporting information, p. 2658 - 2661 (2014/03/21)
Asymmetric intramolecular direct hydroarylation of α-ketoamides gives various types of optically active 3-substituted 3-hydroxy-2-oxindoles in high yields with complete regioselectivity and high enantioselectivities (84-98 % ee). This is realized by the use of the cationic iridium complex [Ir(cod) 2](BArF4) and the chiral O-linked bidentate phosphoramidite (R,R)-Me-BIPAM. Carbon's got a brand new bond: Asymmetric intramolecular direct hydroarylation of α-ketoamides gives various optically active 3-substituted 3-hydroxy-2-oxindoles in high yields with complete regioselectivity and high enantioselectivities. This is realized by the use of an asymmetric cationic iridium complex formed in situ (see Scheme).
