5445-35-2Relevant academic research and scientific papers
Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo-Organomagnesium Anilides
Colas, Kilian,Kohlhepp, Stefanie V.,Mendoza, Abraham,V. D. dos Santos, A. Catarina
supporting information, (2022/02/02)
The synthesis of ketones through addition of organometallic reagents to aliphatic carboxylic acids is a straightforward strategy that is limited to organolithium reagents. More desirable Grignard reagents can be activated and controlled with a bulky aniline-derived turbo-Hauser base. This operationally simple procedure allows the straightforward preparation of a variety of aliphatic and perfluoroalkyl ketones alike from functionalized alkyl, aryl and heteroaryl Grignard reagents.
Mild and direct conversion of esters to morpholine amides using diisobutyl(morpholino)aluminum: Application to efficient one-pot synthesis of ketones and aldehydes from esters
Jeon, Ah Ram,Kim, Min Eai,Park, Jae Kyo,Shin, Won Kyu,An, Duk Keun
, p. 4420 - 4424 (2014/06/10)
Morpholine amide intermediates, which are easily prepared by aminolysis of various esters with diisobutyl(morpholino)aluminum, react with organolithium and reducing agents (DIBALH or LDBMA) without isolation of the aminolysis intermediates to give ketones in 83-95% yields and aldehydes quantitatively.
Cyanocuprates convert carboxylic acids directly into ketones
Genna, Douglas T.,Posner, Gary H.
supporting information; experimental part, p. 5358 - 5361 (2011/12/15)
Carboxylic acids were converted directly in 56-99% yields into methyl, n-butyl, and isopropyl ketones using excess cyanocuprates R2CuLi 3 LiCN. A substrate with a stereocenter α to the carboxylic acid was converted into ketones with very little loss of enantiomeric purity. A variety of functional groups were tolerated including aryl bromides. This direct transformation of a carboxylic acid into ketone with minimal tertiary alcohol formation is proposed to involve a relatively stable copper ketal tetrahedral intermediate.
Empirical method for predicting enantioselectivity in catalytic reactions: demonstration with lipase and oxazaborolidine
Ema, Tadashi,Ura, Norichika,Yoshii, Masataka,Korenaga, Toshinobu,Sakai, Takashi
experimental part, p. 9583 - 9591 (2010/01/06)
We derived a novel equation capable of predicting the degree of enantioselectivity in a catalytic reaction without any knowledge of the reaction mechanism and/or the transition-state structure, and tested the validity of this equation by changing substrates systematically in the lipase or oxazaborolidine-catalyzed reactions. A good correlation was observed between the predicted and observed E values, and the stereochemistry of the products could be predicted correctly in most cases (28 out of 30).
The Mn(Salen)-catalyzed oxidative kinetic resolution of secondary alcohols: reaction development and scope
Cheng, Qigan,Deng, Fanguo,Xia, Chungu,Sun, Wei
experimental part, p. 2359 - 2362 (2009/04/11)
A series of chiral Mn(Salen) complexes have been synthesized and submitted to the kinetic resolution of secondary alcohols bearing a large hindrance in the biphasic system, which is composed of water and CH2Cl2. After evaluating the appropriate complex, additive, and other conditions, chiral secondary alcohols were obtained with enantiomeric excesses of up to 98.6% in 6 min.
Direct and efficient one-pot preparation of ketones from aldehydes using N-tert-butylphenylsulfinimidoyl chloride
Crawford, James J.,Henderson, Kenneth W.,Kerr, William J.
, p. 5073 - 5076 (2007/10/03)
(Chemical Equation Presented) A general, one-pot process has been established to prepare ketones from aldehydes using N-tert- butylphenylsulfinimidoyl chloride. By employing the developed protocol, a range of unsymmetrical ketones has been prepared in good yields from aldehydes in one simple synthetic operation.
A convenient preparation of unsymmetrical ketones from borinates using phase transfer catalysis
Guo, Feng,Huang, Shiwen,Shan, Zixing,Zhao, Dejie
, p. 280 - 281 (2007/10/03)
Unsymmetrical ketones were prepared from borinates via the insertion of dichlorocarbene into the C-B bond under solid-liquid phase transfer catalysis conditions and oxidation with alkaline hydrogen peroxide in 50-78% yields.
One-pot synthesis of ketones using N-methoxy-N-methyl-2-pyridyl urethane
Lee, Na Ra,Lee, Jae In
, p. 1249 - 1255 (2007/10/03)
The one-pot reaction of N-methoxy-N-methyl-2-pyridyl urethane with Grignard and organolithium reagents provided an efficient method for the preparation of unsymmetrical ketones.
Salt effects on the reactivity and the stability of organomanganese reagents
Cahiez, Gerard,Razafintsalama, Lynah,Laboue, Blandine,Chau, Francois
, p. 849 - 852 (2007/10/03)
The reactivity and the stability of organomanganese reagents prepared from the ate complexes MnX2·2LiBr (X= Br,I) and MnCl2·R4NX (X= Br, Cl) were studied. The preparation and the use for synthetic applications of stable sec- and tert-alkylmanganese bromides in ether as well as the acylation of RMnCl by R'COOCOOEt in THF were successfully achieved for the first time.
Reactions of in situ formed acyl tributylphosphonium ions with Grignard reagents as an effective route to ketones from acid chlorides
Maeda, Hatsuo,Okamoto, Junko,Ohmori, Hidenobu
, p. 5381 - 5384 (2007/10/03)
The reactions of acyl tributylphosphonium ions in situ generated from acid chlorides and Bu3P in THF at -22°C with primary alkyl and arylmagnesium halides have proved to be a convenient and simple procedure to prepare ketones from acid chloride in one-pot.
