314248-94-7Relevant academic research and scientific papers
Iron-Catalyzed Acyl Migration of Tertiary α-Azidyl Ketones: Synthetic Approach toward Enamides and Isoquinolones
Yang, Tonghao,Fan, Xing,Zhao, Xiaopeng,Yu, Wei
supporting information, p. 1875 - 1879 (2018/04/16)
This paper reports that tertiary α-azidyl phenyl ketones can be transformed into enamides by treatment with FeBr2 at elevated temperature in DMF. The reaction proceeds via 1,2-benzoyl migration from α-carbon to the nitrogen atom, accompanied by expulsion of a nitrogen molecule. This protocol is suitable for the synthesis of N-(cyclopent-1-en-1-yl)benzamides, N-(cyclohex-1-en-1-yl)benzamides, and N-benzoyl-α-methyl enamines and provides a convenient approach toward isoquinolones.
Vanadium-catalyzed oxidative bromination promoted by Br?nsted acid or Lewis acid
Kikushima, Kotaro,Moriuchi, Toshiyuki,Hirao, Toshikazu
experimental part, p. 6906 - 6911 (2010/09/18)
The oxidative bromination of arenes was induced by a vanadium catalyst in the presence of a bromide salt and a Br?nsted acid or a Lewis acid under molecular oxygen, which provides an eco-friendly bromination method as compared with a conventional bromination one with bromine. This catalytic reaction could be applied to the bromination of alkenes and alkynes to give the corresponding vic-bromides. Use of aluminum halide as a Lewis acid in place of a Br?nsted acid was demonstrated to provide a more practical protocol for the oxidative bromination. From ketones, α-bromination products were obtained. AlBr3 was found to serve as both a bromide source and a Lewis acid to induce the bromination smoothly. 51V NMR experiment showed that this catalytic bromination is likely to depend on the redox cycle of a vanadium catalyst under molecular oxygen.
Stereoselectivity in reactions of amino acids catalyzed by pyridoxal derivatives carrying rigidly-attached chirally-mounted basic groups - Transamination, racemization, decarboxylation, retro-aldol reaction, and aldol condensation
Liu, Lei,Rozenman, Mary,Breslow, Ronald
, p. 3973 - 3979 (2007/10/03)
A tetrahydroquinoline ring was used to mount the critical functional groups of pyridoxal, and also two examples of rigidly held chirally mounted basic groups. They were able to selectively catalyze decarboxylation, aldol reaction, and retro-aldol reaction of amino acids rather than transamination, and with stereoselectivity. In the aldol reaction of glycine with acetaldehyde to synthesize threonine and allo-threonine, one of the catalysts reversed its stereoselectivity when the basic group was protonated. The observed stereoselectivities were all consistent with prediction.
Catalytic enantioselective chlorination and bromination of β-keto esters
Hintermann, Lukas,Togni, Antonio
, p. 2425 - 2435 (2007/10/03)
The Ti(TADDOLato) complexes dichloro[(4R,5R)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dim ethanolato(2 -)-O,O']titanium ((R)-1a) and dichloro[(4R,5R)-2,2-dimethyl-α,α,α',α'-tetra(naphthalen-1-yl)-1,3-dioxol ane-4,5-dimethanolato(2-)-O,O']titan
Reactions of benzocyclic β-keto esters with sulfonyl azides. 2. Further insight into the influence of azide structure and solvent on the reaction course
Benati, Luisa,Nanni, Daniele,Spagnolo, Piero
, p. 5132 - 5138 (2007/10/03)
The reactions of 2-ethoxycarbonyl-1-benzosuberone with 4- methoxybenzenesulfonyl, 2,4,6-triiso-propylbenzenesulfonyl, methanesulfonyl, and trifluoromethanesulfonyl azide, in the presence of triethylamine, have been investigated in N,N-dimethylformamide, a
