ChemInform Abstract: Copper Catalyzed Enantioselective Alkylation of Pyrrole with β,γ-Unsaturated α-Ketoesters: Application to One-Pot Construction of the Seven-Membered Ring by Merging a Gold Catalysis.

ChemInform ◽  
2016 ◽  
Vol 47 (2) ◽  
Author(s):  
Yanbin Hu ◽  
Yanan Li ◽  
Sheng Zhang ◽  
Chong Li ◽  
Lijun Li ◽  
...  
Keyword(s):  
Gold Catalysis ◽  
Membered Ring ◽  
One Pot ◽  
Enantioselective Alkylation

Merging gold catalysis, organocatalytic oxidation, and Lewis acid catalysis for chemodivergent synthesis of functionalized oxazoles from N-propargylamides

2017 ◽  
Vol 53 (75) ◽  
pp. 10366-10369 ◽  
Author(s):  
Shaoyu Mai ◽  
Changqing Rao ◽  
Ming Chen ◽  
Jihu Su ◽  
Jiangfeng Du ◽  
...  
Keyword(s):  
Transition Metal ◽  
Lewis Acid ◽  
Lewis Acids ◽  
Acid Catalysis ◽  
Gold Catalysis ◽  
One Pot ◽  
Catalytic Systems ◽  
One Pot Synthesis ◽  
The One ◽  
Cationic Gold

Novel catalytic systems consisting of cationic gold complexes, N-hydroxyphthalimide (NHPI), and transition-metal-based Lewis acids have been developed for the one-pot synthesis of functionalized oxazoles.

Diverse privileged N-polycyclic skeletons accessed from a metal-free cascade cyclization reaction

2021 ◽  
Vol 19 (37) ◽  
pp. 8086-8095
Author(s):  
Wenzhong Li ◽  
Yu Wang ◽  
Huijing Qi ◽  
Ran Shi ◽  
Jiazhu Li ◽  
...  
Keyword(s):  
Membered Ring ◽  
Cyclization Reaction ◽  
One Pot ◽  
Metal Free ◽  
Cascade Cyclization ◽  
One Pot Synthesis ◽  
Ring Compounds

Metal-free cascade cyclization of 2-acylbenzoic acids with amines provided a one-pot synthesis of diverse isoindoloisoquinoline and benzoindolizinoindole derivatives, which were subsequently used to produce nitrogen-containing nine-membered ring compounds.

Stereocontrolled C-O Ring Construction: The Fuwa/Sasaki Synthesis of Attenol A

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Gold Catalysis ◽  
Membered Ring ◽  
Allylic Alcohol ◽  
State University ◽  
Prins Cyclization ◽  
University Of Florida ◽  
University Of Pittsburgh ◽  
Colorado State University ◽  
Institute Of Technology ◽  
The University

Since five-membered ring ethers often do not show good selectivity on equilibration, single diastereomers are best formed under kinetic control. Aaron Aponick of the University of Florida demonstrated (Organic Lett. 2008, 10, 669) that under gold catalysis, the allylic alcohol 1 cyclized to 2 with remarkable diastereocontrol. Six-membered rings also formed with high cis stereocontrol. Ian Cumpstey of Stockholm University showed (Chem. Commun. 2008, 1246) that with protic acid, allylic acetates such as 3 cyclized with clean inversion at the allylic center, and concomitant debenzylation. J. Stephen Clark of the University of Glasgow found (J. Org. Chem. 2008, 73, 1040) that Rh catalyzed cyclization of 5 proceeded with high selectivity for insertion into Ha, leading to the alcohol 6. Saumen Hajra of the Indian Institute of Technology, Kharagpur took advantage (J. Org. Chem. 2008, 73, 3935) of the reactivity of the aldehyde of 7, effecting selective addition of 7 to 8, to deliver, after reduction, the lactone 9. Tomislav Rovis of Colorado State University observed (J. Org. Chem. 2008, 73, 612) that 10 could be cyclized selectively to either 11 or 12. Nadège Lubin-Germain, Jacques Uziel and Jacques Augé of the University of Cergy- Pontoise devised (Organic Lett. 2008, 10, 725) conditions for the indium-mediated coupling of glycosyl fluorides such as 13 with iodoalkynes such as 14 to give the axial C-glycoside 15. Katsukiyo Miura and Akira Hosomi of the University of Tsukuba employed (Chemistry Lett. 2008, 37, 270) Pt catalysis to effect in situ equilibration of the alkene 16 to the more stable regioisomer. Subsequent condensation with the aldehyde 17 led via Prins cyclization to the ether 18. Paul E. Floreancig of the University of Pittsburgh showed (Angew. Chem. Int. Ed. 2008, 47, 4184) that Prins cyclization could be also be initiated by oxidation of the benzyl ether 19 to the corresponding carbocation. Chan-Mo Yu of Sungkyunkwan University developed (Organic Lett. 2008, 10, 265) a stereocontrolled route to seven-membered ring ethers, by Pd-mediated stannylation of allenes such as 21, followed by condensation with an aldehyde.

scholarly journals One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis

ACS Catalysis ◽  
2014 ◽  
Vol 4 (2) ◽  
pp. 634-638 ◽  
Author(s):  
David M. Barber ◽  
Andrej Ďuriš ◽  
Amber L. Thompson ◽  
Hitesh J. Sanganee ◽  
Darren J. Dixon
Keyword(s):  
Gold Catalysis ◽  
One Pot

scholarly journals First insights into the synthesis of carbo-phospholane and carbo-phospholene oxides

2015 ◽  
Vol 3 (2) ◽  
pp. 80-88 ◽  
Author(s):  
Luc Maurette ◽  
Catherine Saccavini ◽  
Valérie Maraval ◽  
Remi Chauvin
Keyword(s):  
31P Nmr ◽  
Membered Ring ◽  
Yield Reduction ◽  
One Pot ◽  
Alternative Strategies ◽  
Heterocyclic Series ◽  
Preliminary Results ◽  
Nmr Characterization

Fifteen-membered ring carbo-mers of five-membered rings are considered in the heterocyclic series of the phosphole oxide and less unsaturated parents. The synthesis of the first carbo-phospholane oxides is achieved by a [14+1] two-step/one-pot macrocyclization route with 86 % yield. Reduction of the latter phosphora-[5]pericyclyne with SnCl­2 allowed consistent 1H and 31P NMR characterization of the corresponding carbo-phospholene, produced with 11 % yield. The ultimate carbo-phosphole oxide could not be isolated, but preliminary results on alternative strategies towards this 14 pz-electron Hückel carbo-aromatic are reported.

scholarly journals Application of One-Pot Three-Component Condensation Reaction for the Synthesis of New Organophosphorus–Sulfur Macrocycles

Synlett ◽  
2018 ◽  
Vol 29 (11) ◽  
pp. 1496-1501 ◽  
Author(s):  
J. Woollins ◽  
Guoxiong Hua ◽  
David Cordes ◽  
Alexandra Slawin
Keyword(s):  
Multicomponent Reaction ◽  
Room Temperature ◽  
Condensation Reaction ◽  
Synthesis Method ◽  
Membered Ring ◽  
One Pot ◽  
X Ray ◽  
Efficient Approach ◽  
Mild Conditions ◽  
Sulfur Heterocycles

An efficient approach has been developed for the synthesis of new phosphorus–sulfur heterocycles by a one-pot three-component condensation reaction of a four-membered-ring thionation reagent [Lawesson’s reagent or its ferrocene analogue (2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide)], an alkane- or arenedithiol, and a dihaloalkane at room temperature in the presence of triethylamine. The simple synthesis method with mild conditions (room temperature and normal reactant concentrations) enhances further the application of the multicomponent reaction in the preparation of novel phosphorus–sulfur heterocycles. Six representative X-ray structures confirmed the formation of these macrocycles.

Multicomponent synthesis of polysubstituted γ-butyrolactones under Barbier-like conditions

2010 ◽  
Vol 83 (3) ◽  
pp. 621-631 ◽  
Author(s):  
Camille Le Floch ◽  
Erwan Le Gall ◽  
Eric Léonel
Keyword(s):  
Acid Methyl Ester ◽  
Conjugate Addition ◽  
Membered Ring ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Acid Methyl ◽  
Aryl Bromides ◽  
The One ◽  
Dimethyl Itaconate

The one-pot, three-component synthesis of 2,3-di- and 2,2,3-trisubstituted-3-methoxycarbonyl-γ-butyrolactones starting from aryl bromides, dimethyl itaconate, and aldehydes or ketones is described. The cobalt-catalyzed domino process formally involves the in situ metallation of an aromatic bromide, a conjugate addition onto dimethyl itaconate, an aldolization reaction with a carbonyl compound, and a final cyclization into a five-membered ring lactone. This procedure is applied to the concise synthesis of a range of polyfunctionalized γ-butyrolactones displaying a paraconic acid methyl ester subunit.

When gold meets chiral Brønsted acid catalysts: extending the boundaries of enantioselective gold catalysis

2014 ◽  
Vol 50 (96) ◽  
pp. 15124-15135 ◽  
Author(s):  
Suleman M. Inamdar ◽  
Ashok Konala ◽  
Nitin T. Patil
Keyword(s):  
Gold Catalysts ◽  
Gold Catalysis ◽  
Acid Catalysts ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
One Pot ◽  
Catalytic Systems ◽  
Brönsted Acid ◽  
Chiral Bronsted Acid ◽  
Bronsted Acid Catalysts

This review describes the development in the use of Au(i)/Brønsted acid binary catalytic systems to enable an enantioselective transformation in one-pot that cannot be achieved by gold catalysts alone.

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