64274-26-6Relevant articles and documents
Asymmetric Transfer Hydrogenation: Dynamic Kinetic Resolution of α-Amino Ketones
Gediya, Shweta K.,Clarkson, Guy J.,Wills, Martin
, p. 11309 - 11330 (2020/10/12)
A series of α-amino ketones were reduced using asymmetric transfer hydrogenation (ATH) through a dynamic kinetic resolution (DKR). The protecting group was matched to the reducing agent, and following optimization, a series of substrates were investigated, giving products in high diastereoselectivity, over 99% ee in several cases and full conversion. The methodology was applied to the enantioselective synthesis of an MDM2-p53 inhibitor precursor.
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.
Direct Catalytic Chemoselective α-Amination of Acylpyrazoles: A Concise Route to Unnatural α-Amino Acid Derivatives
Tokumasu, Keisuke,Yazaki, Ryo,Ohshima, Takashi
supporting information, p. 2664 - 2669 (2016/03/12)
A direct copper-catalyzed highly chemoselective α-amination is described. Acylpyrazole proved to be a highly efficient enolate precursor of a carboxylic acid oxidation state substrate, while preactivation by a stoichiometric amount of strong base has been used in catalytic α-aminations. The simultaneous activation of both coupling partners, enolization and metal nitrenoid formation, was crucial for obtaining the product, and wide functional group compatibility highlighted the mildness of the present catalysis. The bidentate coordination mode was amenable to highly chemoselective activation over ketone and much more acidic nitroalkyl functionality. Deuterium exchange experiments clearly demonstrated that exclusive enolization of acylpyrazole was achieved without the formation of a nitronate. The present catalysis was applied to late-stage α-amination, allowing for concise access to highly versatile α-amino acid derivatives. The product could be transformed into variety of useful building blocks.
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.
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.
The reaction of [N-(p-toluenesulfonyl)imino]phenyliodinane with enol silanes
Lim, Byeong-Woo,Ahn, Kwang-Hyun
, p. 3407 - 3412 (2007/10/03)
[N-(p-Toluenesulfonyl)imino]phenyliodinane reacts with enol silanes to provide α-tosylamino carbonyl compounds.
Development of the copper-catalyzed olefin aziridination reaction
Evans, David A.,Faul, Margaret M.,Bilodeau, Mark T.
, p. 2742 - 2753 (2007/10/02)
Soluble Cu(I) and Cu(II) triflate and perchlorate salts are efficient catalysts for the aziridination of olefins employing (N-(p-tolylsulfonyl)imino)phenyliodinane, PhI=NTs, as the nitrene precursor. Electron-rich as well as electron-deficient olefins und
