58107-57-6Relevant academic research and scientific papers
Synthesis of Optically Active 2,3-Disubstituted Indoline -Derivatives through Cycloaddition Reactions between Benzynes and α,β-Unsaturated γ-Aminobutyronitriles
Ikawa, Takashi,Sumii, Yuta,Masuda, Shigeaki,Wang, Ding,Emi, Yuto,Takagi, Akira,Akai, Shuji
supporting information, p. 530 - 536 (2018/01/17)
We report a method for synthesizing optically active 2,3-disubstituted indolines by the cycloaddition reaction of benzynes with various 4-[(4-toluenesulfonyl)amino]-(E)-but-2-enenitriles, which are readily prepared from the corresponding l -amino acid der
Photoactivated N-Acyliminoiodinanes Applied to Amination: an ortho-Methoxymethyl Group Stabilizes Reactive Precursors
Kobayashi, Yusuke,Masakado, Sota,Takemoto, Yoshiji
supporting information, p. 693 - 697 (2018/01/17)
N-Acyliminoiodinanes were characterized for the first time by X-ray structural analysis. The ortho-methoxymethyl group and the carbonyl oxygen coordinate to the iodine atom of the iminoiodinane. Activation of the N-acyliminoiodinane was achieved by photoirradiation at 370 nm, thereby enabling reaction with various silyl enol ethers to give α-aminoketone derivatives in good to high yield. N-sulfonyliminoiodinanes bearing ortho substituents were used in photoinduced amination.
Flexible stereoselective functionalizations of ketones through umpolung with hypervalent iodine reagents
Mizar, Pushpak,Wirth, Thomas
supporting information, p. 5993 - 5997 (2014/06/10)
The functionalization of carbonyl compounds in the α-position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or "umpolung", we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel retrosynthetic planning and rapid assembly of structures previously accessible only by multistep sequences. A Nu approach: An efficient α-functionalization of ketones with a range of simple and useful nucleophiles is possible by using hypervalent iodine reagents (see scheme; Nu′ can be the Nu itself or a protected form of this nucleophile group).
O-alkoxyphenyliminoiodanes: Highly efficient reagents for the catalytic aziridination of alkenes and the metal-free amination of organic substrates
Yoshimura, Akira,Nemykin, Victor N.,Zhdankin, Viktor V.
supporting information; experimental part, p. 10538 - 10541 (2011/11/12)
Efficient nitrene precursors: Highly reactive iminoiodane-based nitrene precursors were prepared from ortho-alkoxyiodobenzenes. Owing to the presence of the ortho-substituent on the phenyl ring, these new iminoiodanes have excellent solubility in organic
Diversity-oriented synthesis based on the dppp-catalyzed mixed double-michael reactions of electron-deficient acetylenes and β-amino alcohols
Fan, Yi Chiao,Kwon, Ohyun
scheme or table, p. 3802 - 3825 (2011/06/24)
In this study, we prepared oxizolidines through 1,3-bis(diphenylphosphino)- propane (DPPP)-catalyzed mixed double-Michael reactions of β-amino alcohols with electron-deficient acetylenes. These reactions are very suitable for the diversity-oriented parallel syntheses of oxizolidines because: (i) they are performed under mild metal-free conditions and (ii) the products are isolated without complicated work-up. To demonstrate the applicability of mixed double-Michael reactions for the preparation of five-membered-ring heterocycles, we prepared 60 distinct oxazolidines from five β-amino alcohols and 12 electron-deficient acetylenes. We synthesized 36 of these 60 oxazolidines in enantiomerically pure form from proteinogenic amino acid-derived β-amino alcohols.
Iron-catalyzed aziridination reactions
Nakanishi, Masafumi,Salit, Anne-Frederique,Bolm, Carsten
body text, p. 1835 - 1840 (2009/07/09)
A small quantity of iron(II) triflate (2.5 to 5 mol%) catalyzes the aziridination reactions of enol silyl ethers with tosylimino(iodo)benzene (PhINTs) in acetonitrile to give α-N-tosylamido ketones by subsequent aziridine ring opening. Olefins are convert
Facile preparation of α-amino ketones from oxidative ring-opening of aziridines by pyridine N-oxide
Luo, Zhi-Bin,Wu, Jing-Yu,Hou, Xue-Long,Dai, Li-Xin
, p. 3428 - 3430 (2008/09/19)
The oxidative ring-opening reaction of a variety of activated aziridines by pyridine N-oxide provided α-amino ketones or α-amino aldehydes in good yields. The Royal Society of Chemistry.
A mild and efficient procedure for the oxidation of epoxides and aziridines using cerium(IV) ammonium nitrate and NBS
Surendra,Srilakshmi Krishnaveni,Rama Rao
, p. 4111 - 4113 (2007/10/03)
The CAN and NBS combination has been used for the first time for the synthesis of versatile α-hydroxy ketones and α-amino ketones from oxiranes/aziridines, respectively, in excellent yields. This method is a direct, one-pot, synthesis under mild conditions using acetonitrile-water (9:1) as solvent.
First osmium-catalysed ketamination of alkenes
Villar, Amparo,Hoevelmann, Claas H.,Nieger, Martin,Muniz, Kilian
, p. 3304 - 3306 (2007/10/03)
Conditions for a first oxidative conversion of alkenes into 2-amino ketones are described, which yield racemic products within a direct oxidation pathway and 2-amino ketones with up to 99% enantiomeric excess from the corresponding enantiopure amino alcohols. The Royal Society of Chemistry 2005.
Cu-exchanged Y-zeolite: A heterogeneous catalyst for the synthesis of α-aminoketones
Phukan,Sudalai
, p. 515 - 517 (2007/10/03)
Cu-zeolitc catalyzes the amination of silyl enol ethers using Phl=NTs producing α-amino ketones in good yields.
