17529-98-5Relevant academic research and scientific papers
Pd-Catalyzed Heck-Type Reaction: Synthesizing Highly Diastereoselective and Multiple Aryl-Substituted P-Ligands
Li, Chong,Qiang, Xiao-Yue,Qi, Zhi-Chao,Cao, Bin,Li, Jing-Yu,Yang, Shang-Dong
, p. 7138 - 7142 (2019)
In this work, an efficient palladium-catalyzed Heck-type reaction was successfully used to synthesize a wide range of monoaryl-or diaryl-substituted P-ligands with excellent yields and diastereoselectivity (up to 98% yield, dr >20:1). The preliminary mechanistic studies demonstrated that it possibly underwent a cationic Heck reaction that was assisted by silver salt, and it revealed the significant role of P(O)Ar2 for excellent yields and diastereoselectivity.
CRYSTAL FORMS AND METHODS OF SYNTHESIS OF (2R, 6R)-HYDROXYNORKETAMINE AND (2S, 6S)-HYDROXYNORKETAMINE
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Paragraph 0258; 0259; 0260, (2019/02/19)
The disclosure provides a method for synthesizing free base forms of (2R,6R)-hydroxynorketamine (HNK) and (2S,6S)-hydroxynorketamine. In an embodiment synthesis of (2R,6R)-hydroxynorketamine (HNK) includes preparation of (R)-norketamine via chiral resolution from racemic norketamine via a chiral resolution with L-pyroglutamic acid. The disclosure also provided crystal forms of the corresponding (2R,6R)-hydroxynorketamine (HNK) and (2S,6S)-hydroxynorketamine hydrochloride salts.
Umpolung-like Cross-coupling of Tosylhydrazones with 4-Hydroxy-2-pyridones under Palladium Catalysis
Katsina, Tania,Papoulidou, Kyriaki Eleni,Zografos, Alexandros L.
supporting information, p. 8110 - 8115 (2019/10/11)
Tosylhydrazones under palladium catalysis were found to perform cross-coupling reactions with 4-hydroxy-2-pyridones. The umpolung-like reactivity, between the α-carbon of tosylhydrazone and the 3-position of the heterocycle, which is observed in the obtai
Palladium-Catalyzed Cross-Coupling of gem-Bis(boronates) with Aryl Halides: An Alternative to Access Quaternary α-Aryl Aldehydes
Zheng, Purui,Zhai, Yujie,Zhao, Xiaoming,Xu, Tao
supporting information, p. 393 - 396 (2019/01/23)
The compounds with a quaternary α-aryl aldehyde skeleton are important units in organic chemistry. Previously, the aryl group and carbonyl group are introduced in a stepwise manner. Herein, a novel route is developed to construct the quaternary α-aryl aldehydes with gem-bis(boronates) as precursors, in which the two groups are installed simultaneously. The gem-bis(boronates) are readily available from ketones; as a result, this methodology provides a more general strategy to produce the quaternary α-aryl aldehydes with broad scopes and synthetic convenience.
Zinc-promoted cyclization of tosylhydrazones and 2-(dimethylamino)malononitrile: An efficient strategy for the synthesis of substituted 1-tosyl-1: H -pyrazoles
Zhang, Bang-Hong,Lei, Lin-Sheng,Liu, Si-Zhan,Mou, Xue-Qing,Liu, Wei-Ting,Wang, Shao-Hua,Wang, Jie,Bao, Wen,Zhang, Kun
supporting information, p. 8545 - 8548 (2017/08/04)
A Zn(OTf)2-promoted cyclization reaction of tosylhydrazones with 2-(dimethylamino)malononitrile has been successfully developed providing an efficient strategy for the synthesis of substituted 1-tosyl-1H-pyrazoles.
One-Pot Synthesis of Spirocyclic or Fused Pyrazoles from Cyclic Ketones: Calcium Carbide as the Carbon Source in Ring Expansion
Yu, Yue,Chen, Yang,Huang, Wei,Wu, Wanqing,Jiang, Huanfeng
, p. 9479 - 9486 (2017/09/23)
N-Tosylhydrazones generated in situ from cyclic ketones smoothly underwent a [3 + 2] cycloaddition to afford saturated spirocyclic pyrazoles and further transformed to the fused analogues via a ring expansion in certain cases. An inexpensive and renewable
Catalyst-free synthesis of spiropyrazolines from chalcones and cyclic ketone N -tosylhydrazones
Wu, Qin-Xi,Li, Hui-Jing,Wang, Hong-Shuang,Zhang, Zhen-Guo,Wang, Chen-Chao,Wu, Yan-Chao
supporting information, p. 243 - 249 (2015/03/05)
Treatment of cyclic ketone N-tosylhydrazones with chalcones in the presence of cesium carbonate at 110 °C affords spiropyrazolines with high selectivity and excellent yields. This protocol possesses many advantages such as readily available and stable sta
Preparation of unsymmetrical ketones from tosylhydrazones and aromatic aldehydes via formyl C-H bond insertion
Allwood, Daniel M.,Blakemore, David C.,Ley, Steven V.
supporting information, p. 3064 - 3067 (2014/06/23)
Preparation of ketones by insertion of diazo compounds into the formyl C-H bond of an aldehyde is an attractive procedure, but use of structurally diverse diazo compounds is hampered by preparation and safety issues. A convenient procedure for the synthesis of unsymmetrical ketones from bench-stable tosylhydrazones and aryl aldehydes is reported. The procedure can be performed in one pot from the parent carbonyl compound and needs only a base, with no additional promoters being required.
Catalytic enantioselective allylboration of propargylic aldehydes
Bhakta, Urmibhusan,Sullivan, Erin,Hall, Dennis G.
supporting information, p. 678 - 683 (2014/02/14)
Homoallylic propargylic alcohols are important building blocks in natural product synthesis. This moiety can be transformed into various other structures by performing other known transformations, which can in turn lead to the synthesis of biologically us
Enantioselective aziridination of cyclic enals facilitated by the fluorine-iminium ion Gauche effect
Molnar, Istvan Gabor,Tanzer, Eva-Maria,Daniliuc, Constantin,Gilmour, Ryan
supporting information, p. 794 - 800 (2014/01/23)
The enantioselective, organocatalytic aziridination of small, medium and macro-cyclic enals is reported using (S)-2-(fluorodiphenyl methyl)-pyrrolidine. Central to the reaction design is the reversible formation of a β-fluoroiminium ion intermediate, which is pre-organised on account of the fluorine-iminium ion gauche effect. This conformational effect positions the fluorine substituent synclinal-endo to the electropositive nitrogen centre thus benefiting from favourable stereoelectronic and electrostatic interactions (σC-H→σC-F*; F δ-···N+). Consequently, one of the shielding groups on the fluorine-bearing carbon atom is positioned above the π-system, forming the basis of an enantioinduction strategy. Treatment of this intermediate with a "nitrene" source furnished a series of novel, optically active aziridines (e.r. up to 99.5:0.5). Further derivatisation of the product aziridines gives facile access to various amino acid derivatives, including β-fluoroamino acids. Crystallographic analyses of both the aziridines and their derivatives are disclosed. Copyright
