76584-03-7Relevant academic research and scientific papers
Manganese=Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2
Gao, Ziwei,Gou, Jing,Hao, Zhe,Hou, Jing,Li, Chaoqun,Li, Gaoqiang,Xing, Qingzhao,Yu, Binxun
, p. 9563 - 9586 (2021/07/20)
Oxidation reactions have been extensively studied in the context of the transformations of biomass=derived furans. However, in contrast to the vast literature on utilizing the stoichiometric oxidants, such as m=CPBA and NBS, catalytic methods for the oxidative furan=recyclizations remain scarcely investigated. Given this, we report a means of manganese=catalyzed oxidations of furan with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide as an environmentally benign oxidant under mild conditions with wide functional group compatibility.
Room-Temperature Guerbet Reaction with Unprecedented Catalytic Efficiency and Enantioselectivity
Lau, Kai Kiat,Liao, Gang,Ng, Teng Wei,Pan, Hui-Jie,Zhao, Yu
supporting information, p. 11384 - 11389 (2020/06/02)
We report herein an unprecedented highly efficient Guerbet-type reaction at room temperature (catalytic TON up to >6000). This β-alkylation of secondary methyl carbinols with primary alcohols has significant advantage of delivering higher-order secondary alcohols in an economical, redox-neutral fashion. In addition, the first enantioselective Guerbet reaction has also been achieved using a commercially available chiral ruthenium complex to deliver secondary alcohols with moderate yield and up to 92 % ee. In both reactions, the use of a traceless ketone promoter proved to be beneficial for the catalytic efficiency.
Visible-light-mediated achmatowicz rearrangement
Plutschack, Matthew B.,Seeberger, Peter H.,Gilmore, Kerry
supporting information, p. 30 - 33 (2017/11/28)
Visible-light-mediated photoredox catalysis is a viable method to access highly reactive intermediates from cheap, readily available, and shelfstable reagents to perform clean chemical transformations. Here, we report the first photoredox-catalyzed Achmatowicz reaction of furfuryl alcohol derivatives to produce functionalized dihydropyranones while only forming easily separable NaHSO4 as a byproduct. The water solubility of the byproduct facilitates direct Boc-protection of the resulting hemiacetal without the need for column purification. The reaction is very robust and permits the use of various aqueous solutions and light sources including sunlight.
Pseudocine Substitution of 4-(Mesyloxy)-2-cyclopentenones: An Efficient Route to 2,4-Disubstituted 2-Cyclopentenones
West, F. G.,Gunawardena, Gamini
, p. 2402 - 2406 (2007/10/02)
Readily available mesylates 1a-d were found to undergo a novel substitution reaction.In the presence of a variety of nucleophiles, 1a-d underwent a net substitution in which the nucleophile was introduced vicinally (C-3) to the departing mesylate (C-4) and the double bond migrated to C-4/C-5.Lithium bromide, thiophenol, benzylamine, sodium azide, and the potassium salt of dimethyl malonate all led to substitution products in good yield.The reaction is thought to proceed by way of initial conjugate addition of the nucleophile, followed by enolate equilibration and β-elimination of mesylate.
A NEW STRATEGY FOR THE ENANTIOSELECTIVE SYNTHESIS OF THE δ-LACTONE MOIETY OF COMPACTIN AND MEVINOLIN
Mico, Antonella De,Piancatelli, Giovanni,Cacurri, Stefania,Lappa, Sperandina
, p. 415 - 419 (2007/10/02)
A new strategy for the preparation of optically active lactone analogues of the inhibitors of hydroxy-methylglutaryl-coenzyme A reductase is outlined.The lactone moiety has been elaborated by enzymatic resolution with porcine pancreas lipase of racemic 4-
