13013-02-0Relevant articles and documents
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Leonard,Felley
, p. 2537,2542 (1950)
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N-heterocyclic carbene catalyzed C-C bond cleavage in redox esterifications of chiral formylcyclopropanes
Sohn, Stephanie S.,Bode, Jeffrey W.
, p. 6021 - 6024 (2006)
(Chemical Equation Presented) A clean break: An N-heterocyclic carbene catalyzes the ring-opening of chiral non-racemic formylcyclopropanes, with simultaneous oxidation of the aldehyde function and without the need for stoichiometric reagents. The activated carboxylate intermediate is trapped by a variety of nucleophiles, thus leading to chiral esters, thioesters, or carboxylic acids (see scheme; DBU = 1,8-diazabicyclo-[5.4.0]undec-7-ene, EWG = electron-withdrawing group, Nu = nucleophile.)
Synthesis and antiarrhythmic activity of (1,3-dimethyl-5-nitro-5- hexahydropyrimidinyl)-propionic acid methyl ester
Shakirov,Yarmukhamedov,Vlasova,Baibulatova,Khisamutdinova,Gabdrakhmanova,Karachurina,Baschenko
, p. 29 - 31 (2006)
(1,3-Dimethyl-5-nitro-5-hexahydropyrimidinyl)propionic acid methyl ester (I) was obtained with a 83% yield using a Mannich type reaction of 4-nitrobutanoic acid methyl ester with excess formalin and methylamine. It was found that compound I possesses low toxicity and shows antiarrhythmic activity on models of arrhythmia induced by intravenous injections of calcium chloride and aconitine in rats.
Oxidative Amidation of Nitroalkanes with Amine Nucleophiles using Molecular Oxygen and Iodine
Li, Jing,Lear, Martin J.,Kawamoto, Yuya,Umemiya, Shigenobu,Wong, Alice R.,Kwon, Eunsang,Sato, Itaru,Hayashi, Yujiro
supporting information, p. 12986 - 12990 (2015/11/02)
The formation of amides and peptides often necessitates powerful yet mild reagent systems. The reagents used, however, are often expensive and highly elaborate. New atom-economical and practical methods that achieve such goals are highly desirable. Ideally, the methods should start with substrates that are readily available in both chiral and non-chiral forms and utilize cheap reagents that are compatible with a wide variety of functional groups, steric encumberance, and epimerizable stereocenters. A direct oxidative method was developed to form amide and peptide bonds between amines and primary nitroalkanes simply by using I2 and K2CO3 under O2. Contrary to expectations, a 1:1 halogen-bonded complex forms between the iodonium source and the amine, which reacts with nitronates to form α-iodo nitroalkanes as precursors to the amides.
Catalytic Asymmetric Synthesis of Isoxazolines from Silyl Nitronates
Han, Xiaoyu,Dong, Li,Geng, Caiwei,Jiao, Peng
supporting information, p. 3194 - 3197 (2015/07/15)
1,3-Dipolar cycloadditions of triisopropylsilyl nitronates and 2-alkylacroleins produced isoxazolines bearing a chiral quaternary center in high yields and enantioselectivities with the aid of a chiral oxazaborolidine catalyst. One chiral isoxazoline product was converted to (R)-(+)-Tanikolide in 9 steps in a total yield of 43%. (Chemical Equation Presented).