scholarly journals Enantioselective 1,4-addition of cyclopropylboronic acid catalyzed by rhodium/chiral diene complexes

2015 ◽  
Vol 51 (40) ◽  
pp. 8528-8531 ◽  
Author(s):  
Ryosuke Takechi ◽  
Takahiro Nishimura
Keyword(s):  
Asymmetric Addition ◽  
Acid Catalyzed ◽  
High Yields

Rhodium-catalyzed asymmetric addition of cyclopropylboronic acids to electron-deficient alkenes proceeded to give high yields of the corresponding 1,4-addition products with high enantioselectivity.

Efficient Synthesis of Diarylmethylamines via Lewis Acid Catalyzed Friedel–Crafts Reactions of Donor–Acceptor Aziridines with N,N-Dialkylanilines

Synthesis ◽  
2019 ◽  
Vol 52 (02) ◽  
pp. 281-289
Author(s):  
Yerin Kim ◽  
Yong Il Kwon ◽  
Sung-Gon Kim
Keyword(s):  
Lewis Acid ◽  
Efficient Synthesis ◽  
Broad Scope ◽  
Donor Acceptor ◽  
Acid Catalyzed ◽  
High Yields

A method for efficient and mild synthesis of diarylmethylamine scaffold, via Lewis acid catalyzed Friedel–Crafts reaction of donor­–acceptor aziridines with N,N-dialkylanilines to afford a biologically important diarylmethylamine derivatives in high yields (up to 88%), is presented. This reaction is suitable for the synthesis of various diarylmethylamine derivatives and has a broad scope for electron-rich arenes, including dimethoxybenzene.

SiO2·12WO3·24H2O: a Highly Efficient Catalyst for the Synthesis of 5-Arylidene Barbituric Acid in the Presence of Water

2009 ◽  
Vol 62 (4) ◽  
pp. 353 ◽  
Author(s):  
Ji-Tai Li ◽  
Ming-Xuan Sun
Keyword(s):  
Room Temperature ◽  
Barbituric Acid ◽  
Aqueous Media ◽  
Aromatic Aldehydes ◽  
Efficient Catalyst ◽  
Highly Efficient ◽  
Efficient Route ◽  
Acid Catalyzed ◽  
High Yields

The condensation of aromatic aldehydes and barbituric acid catalyzed by SiO2·12WO3·24H2O in aqueous media at room temperature gave 5-arylidene barbituric acid in high yields with or without the use of ultrasound, providing a simple and efficient route to synthesis of these compounds.

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

Synthesis ◽  
2020 ◽  
Vol 52 (21) ◽  
pp. 3263-3271
Author(s):  
Andrey V. Smolobochkin ◽  
Almir S. Gazizov ◽  
Nazerke K. Otegen ◽  
Julia K. Voronina ◽  
Anna G. Strelnik ◽  
...  
Keyword(s):  
Substitution Reaction ◽  
Electrophilic Substitution ◽  
Biologically Active ◽  
Electrophilic Substitution Reaction ◽  
Reaction Sequence ◽  
Active Compounds ◽  
Acid Catalyzed ◽  
High Yields ◽  
Nucleophilic Cyclization ◽  
Mechanism Of The Reaction

Imidazolidin-2-one and 1,3-benzodiazepin-2-one scaffolds are structural motifs of many biologically active compounds. Herein, we report a highly regioselective acid-catalyzed intramolecular nucleophilic cyclization/intermolecular electrophilic substitution reaction sequence of (2,2-dialkoxyethyl)ureas. The reaction benefits from readily available starting materials, a simple workup procedure, moderate to high yields of target compounds, and provides a convenient entry to previously unknown 4-(het)arylimidazolidinones and 5-(het)arylbenzodiazepinones. The proposed mechanism of the reaction is also discussed.

Lewis Acid-Catalyzed Rearrangement of Fluoroalkylated Propargylic Alcohols: An Alternative Approach to β-Fluoroalkyl-α,β-enones

Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 356-360 ◽  
Author(s):  
Manickavasakam Ramasamy ◽  
Hui-Chang Lin ◽  
Sheng-Chu Kuo ◽  
Min-Tsang Hsieh
Keyword(s):  
Lewis Acid ◽  
Propargylic Alcohols ◽  
Alternative Approach ◽  
Acid Catalyzed ◽  
High Yields ◽  
High Stereoselectivity

A practical Lewis acid-catalyzed Meyer–Schuster rearrangement of fluoroalkylated propargylic alcohols, leading to a series of β-fluoroalkyl-α,β-enones, is developed. The methodology reported herein features moderate to high yields and high stereoselectivity in the synthesis of β-alkyl-β-fluoroalkyl-α,β-enones.

Friedel–Crafts alkylation of heteroarenes and arenes with indolyl alcohols for construction of 3,3-disubstituted oxindoles

RSC Advances ◽  
2015 ◽  
Vol 5 (123) ◽  
pp. 101713-101717 ◽  
Author(s):  
Xiaoxiao Wang ◽  
Jian Liu ◽  
Lubin Xu ◽  
Zhihui Hao ◽  
Liang Wang ◽  
...  
Keyword(s):  
Reaction Conditions ◽  
Camphorsulfonic Acid ◽  
Acid Catalyzed ◽  
High Yields

An intriguing camphorsulfonic acid catalyzed Friedel–Crafts alkylation of arenes with indolyl alcohols has been developed featuring mild reaction conditions, wide substrate scope and high yields.

scholarly journals Organocatalytic asymmetric selenofunctionalization of tryptamine for the synthesis of hexahydropyrrolo[2,3-b]indole derivatives

2013 ◽  
Vol 9 ◽  
pp. 1559-1564 ◽  
Author(s):  
Qiang Wei ◽  
Ya-Yi Wang ◽  
Yu-Liu Du ◽  
Liu-Zhu Gong
Keyword(s):  
Phosphoric Acid ◽  
Indole Derivatives ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
High Yields

A chiral phosphoric acid-catalyzed selenofunctionalization of tryptamine derivatives provides access to 3a-(phenylselenyl)-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole derivatives in high yields and with synthetically useful levels of enantioselectivity (up to 89% ee).

Synthesis of Pentacoordinated Spiro[4,4]phosphoranes by Reaction of Cyclic Phosphazenyl Anions with Epoxides. Study of their P-Remote Functionalization and Hydrolysis

Synthesis ◽  
2021 ◽  
Author(s):  
Pablo Manuel Sansores Peraza ◽  
Jesús García López ◽  
Yolanda Navarro ◽  
María José Iglesias ◽  
Fernando López Ortiz
Keyword(s):  
Benzoic Acid ◽  
Alkaline Hydrolysis ◽  
Phosphorus Atom ◽  
Bidentate Ligand ◽  
New Family ◽  
Acid Catalyzed ◽  
High Yields ◽  
Hydrolysis Of ◽  
Carbon Based

The synthesis of a new family of pentacoordinated spiro[4,4]phosphoranes stabilized by the ortho-benzamide bidentate ligand (oBA,-C6H4-2-C(O)NH-) through reaction of Cα -Cortho-dilithiated phosphazenes with oxiranes is reported. Mixtures of epimers that differ in configuration at the phosphorus atom were obtained with moderate to high yields and diastereoselectivities. C3-disubstituted derivatives could be separated, which provided access to enantiopure products arising from the reaction with (R)-2-phenyloxirane. Stereomutation was observed by heating the spirophosphoranes at 100 ºC. Directed ortho lithiation of spirophoshoranes followed by electrophilic quench reactions including carbon-based and heteroatom-based electrophiles afforded derivatives functionalized in remote position with respect to the phosphorus atom. Benzoic acid catalyzed hydrolysis of spirophosphoranes furnished ortho-(hydroxyalkylphosphoryl)benzamides by cleavage of the P‒O and P‒N bonds with retention of the phosphorus configuration. In contrast, alkaline hydrolysis led to the formation of γ-hydroxyphosphinic acids and benzamide.

scholarly journals Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction

2014 ◽  
Vol 10 ◽  
pp. 2892-2896 ◽  
Author(s):  
Chun-Huan Jiang ◽  
Xiantao Lei ◽  
Le Zhen ◽  
Hong-Jin Du ◽  
Xiaoan Wen ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Reducing Power ◽  
Isomerization Reaction ◽  
Hydride Shift ◽  
Acid Catalyzed ◽  
High Yields

Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolcular [1,5]-hydride shift/isomerization reaction has been realized, using the inherent reducing power of 3-pyrrolines. A series of N-arylpyrrole containing amines are obtained in high yields.

Chiral phosphoric acid catalyzed asymmetric addition of naphthols to para-quinone methides

2016 ◽  
Vol 14 (24) ◽  
pp. 5751-5754 ◽  
Author(s):  
Yuk Fai Wong ◽  
Zhaobin Wang ◽  
Jianwei Sun
Keyword(s):  
Phosphoric Acid ◽  
Quinone Methides ◽  
Asymmetric Addition ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed

An asymmetric addition of naphthols to in situ generated para-quinone methides catalyzed by a chiral phosphoric acid is described.

Lewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines

2013 ◽  
Vol 49 (68) ◽  
pp. 7492 ◽  
Author(s):  
Yingle Liu ◽  
Jiawang Liu ◽  
Yangen Huang ◽  
Feng-Ling Qing
Keyword(s):  
Lewis Acid ◽  
Regioselective Synthesis ◽  
Asymmetric Addition ◽  
Acid Catalyzed
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