17745-32-3Relevant academic research and scientific papers
Preparation of Functionalized Ketones via Low temperature Grignard Reaction
Eberel, Marcel K.,Kahle, Gerard G.
, p. 2303 - 2304 (1980)
δ-Chloroketones and 5-oxo-9-decenoic acid methyl ester were prepared from 5-chlorovaleryl chloride and methyl 4-(chloroformyl)-butyrate via Grignard reaction in tetrahydrofuran at -70 deg C.
Iron-catalyzed oxidative functionalization of C(sp3)-H bonds under bromide-synergized mild conditions
Yu, Han,Zhao, Qixin,Wei, Zheyu,Wu, Zhikang,Li, Qi,Han, Sheng,Wei, Yongge
supporting information, p. 7840 - 7843 (2019/07/12)
An efficient oxidation and functionalization of C-H bonds with an inorganic-ligand supported iron catalyst and hydrogen peroxide to prepare the corresponding ketones was achieved using the bromide ion as a promoter. Preliminary mechanistic investigations indicated that the bromide ion can bind to FeMo6 to form a supramolecular species (FeMo6·2Br), which can effectively catalyze the reaction.
An efficient method for retro-Claisen-type C-C bond cleavage of diketones with tropylium catalyst
Hussein,Huynh,Hommelsheim,Koenigs,Nguyen
supporting information, p. 12970 - 12973 (2018/11/23)
The retro-Claisen reaction is frequently used in organic synthesis to access ester derivatives from 1,3-dicarbonyl precursors. The C-C bond cleavage in this reaction is usually promoted by a number of transition-metal Lewis acid catalysts or organic Br?nsted acids/bases. Herein we report a new convenient and efficient method utilizing the tropylium ion as a mild and environmentally friendly organocatalyst to mediate retro-Claisen-type reactions. Using this method, a range of synthetically valuable substances can be accessed via solvolysis of 1,3-dicarbonyl compounds.
Combined effects on selectivity in Fe-catalyzed methylene oxidation
Chen, Mark S.,White, M. Christina
scheme or table, p. 533 - 571 (2010/10/05)
Methylene C-H bonds are among the most difficult chemical bonds to selectively functionalize because of their abundance in organic structures and inertness to most chemical reagents. Their selective oxidations in biosynthetic pathways underscore the power of such reactions for streamlining the synthesis of molecules with complex oxygenation patterns. We report that an iron catalyst can achieve methylene C-H bond oxidations in diverse natural-product settings with predictable and high chemo-, site-, and even diastereoselectivities. Electronic, steric, and stereoelectronic factors, which individually promote selectivity with this catalyst, are demonstrated to be powerful control elements when operating in combination in complex molecules. This small-molecule catalyst displays site selectivities complementary to those attained through enzymatic catalysis.
Oxidative cleavage of the C-C bond of 3,6-dialkylcyclohexane-1,2-diones by cell suspension cultures of Marchantia polymorpha
Matsuura, Yoshitomo,Chai, Wen,Endoh, Etsuko,Suhara, Jyumpei,Hamada, Hiroki,Horiuchi, C. Akira
, p. 669 - 673 (2007/10/03)
Biotransformation of 3,6-dialkylcyclohexane-1,2-diones by cell suspension cultures of Marchantia polymorpha involves regio-selective oxidative cleavage of the C-C bond to give the corresponding oxocarboxylic acids shortened by one carbon unit. In the case of cyclohexane-1,2-dione, adipic acid was obtained.
Highly regioselective addition of an ester enolate equivalent to α,β-unsaturated ketones: Selective formation of both isomers derived from 1,2- and 1,4-additions using α-stannyl ester with additives
Yasuda,Matsukawa,Okamoto,Sako,Kitahara,Baba
, p. 2149 - 2150 (2007/10/03)
The reaction of α-stannyl ester with α,β-unsaturated ketones in the presence of stannous chloride (SnCl2) and chlorosilanes (Me3SiCl or Me2SiCl2) gave 1,2- and 1,4-addition products, respectively.
Oxidation of 2-substituted cycloalkanones with cerium(IV) sulfate tetrahydrate in alcohols and acetic acid
He, Liangyou,Horiuchi, C. Akira
, p. 2515 - 2521 (2007/10/03)
The reaction of 2-substituted cycloalkanones with cerium(IV) sulfate tetrahydrate (CS) in alcohols and acetic acid gave the corresponding alkyl esters of oxo acids (80-96%) and oxo acids (78-96%), respectively, by oxidative cleavage of the C(R).C=O bond. In the case of 2-iodocycloalkanones in methanol, the dimethyl ester was obtained in good yield. A treatment of 5α-cholestan-3-one with CS in methanol produced 2-acetal 3-ester of 2,3-seco derivative in good yield. The effects of cerium(IV) and copper(II) salts are also discussed.
Asymmetric synthesis with chiral hydrogenolysable amines, ω-imino esters reduction: A diastereoselective route to ω-alkyl lactams
Marx,El Bouz,Celerier,Lhommet
, p. 4307 - 4310 (2007/10/02)
Chiral methylbenzylamine is used to prepare ω-amino esters which are then transformed into ω-alkyl lactams with good diastereoselectivity.
