2,3,6-Tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D-glucopyranosyl bromide
CAS Number:
4753-07-5
Molecular Formula:
C26H35BrO17
Asymmetric synthesis of spiro-structural 2,3-dihydrobenzofurans via the bifunctional phosphonium salt-promoted [4 + 1] cyclization of ortho-quinone methides with α-bromoketones
Literature Information
Publication Date
2019-10-08
DOI
10.1039/C9QO01096C
Impact Factor
5.281
Authors
Song Zhang, Jianke Pan, Hongsu Zhang, Tianli Wang
View Original
Abstract
We report a practical and scalable method for the highly diastereo- and enantio-selective construction of 2,3-dihydrobenzofurans bearing spiro-structures by means of cyclization reactions between ortho-quinone methides and α-bromoketones through bifunctional phosphonium salt catalysis under mild conditions. A variety of spiro-fused 2,3-dihydrobenzofuran derivatives were readily synthesized in high yields with excellent diastereo- and enantio-selectivities (up to >20 : 1 dr and 97% ee). This protocol represents an alternative facile way for preparing biologically important chiral 2,3-dihydrobenzofurans. Moreover, mechanistic observations indicated that the hydrogen bonding interaction between the Brønsted acid moiety of the phosphonium catalyst and the “CO” unit of the quinone is crucial for stereoinduction.
Recommended Journals
Related Literature
The puzzling hyper-fine structure and an accurate equilibrium geometry of succinic anhydride
Michaela K. Jahn, Daniel A. Obenchain, K. P. Rajappan Nair, Jens-Uwe Grabow, Jean Demaison, Peter D. Godfrey, Don McNaughton
2020-02-12
Paper
DOI: 10.1039/C9CP06775B
A methodical study of quantum phase engineering in topological crystalline insulator SnTe and related alloys
Mohsen Yarmohammadi, Kavoos Mirabbaszadeh
2019-08-16
Paper
DOI: 10.1039/C9CP03655E
An electric double layer structure and differential capacitance at the electrode interface of tributylmethylammonium bis(trifluoromethanesulfonyl)amide studied using a molecular dynamics simulation
Seiji Katakura, Naoya Nishi, Kazuya Kobayashi, Tetsuo Sakka
2020-01-28
Paper
DOI: 10.1039/C9CP05297F
A quantum chemical study of hydrogen adsorption on carbon-supported palladium clusters
Lisa Warczinski, Christof Hättig
2019-09-10
Paper
DOI: 10.1039/C9CP04606B
Molecular dynamics investigations of oligosaccharides recognized by family 16 and 22 carbohydrate binding modules
Ruihan Wang
2019-09-05
Paper
DOI: 10.1039/C9CP04673A
Seeking minimum entropy production for a tree-like flow-field in a fuel cell
Marco Sauermoser, Signe Kjelstrup, Bruno G. Pollet, Eirik G. Flekkøy
2020-03-18
Paper
DOI: 10.1039/C9CP05394H
Suppressing triplet decay in quinoidal singlet fission materials: the role of molecular planarity and rigidity
Guangchao Han, Qian Peng
2020-03-09
Paper
DOI: 10.1039/C9CP06987A
You might also like
Compound Q&A
Is 6-(3-Fluorophenyl)picolinic acid (CAS: 887982-40-3) safe?
6-(3-Fluorophenyl)picolinic acid is generally considered safe for laboratory use...
887982-40-36-(3-Fluorophenyl)pi...
Compound Q&A
What industries use (3R)-3-Pyrrolidinol (CAS: 2799-21-5)?
(3R)-3-Pyrrolidinol is used in the pharmaceutical industry as a precursor for dr...
2799-21-5(3R)-3-Pyrrolidinol
Compound Q&A
What precautions should be taken when handling (4R,5R)-4,5-Diethoxycarbonyl-2,2-dimethyldioxolane (CAS: 59779-75-8)?
When handling (4R,5R)-4,5-Diethoxycarbonyl-2,2-dimethyldioxolane (CAS: 59779-75-...
59779-75-8(4R,5R)-4,5-Diethoxy...
Compound Q&A
How is 1-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)ethanone (CAS: 90734-71-7) typically synthesized?
1-(6-Chloroimidazo[1,2-b]pyridazin-3-yl)ethanone is often synthesized via a mult...
90734-71-71-(6-Chloroimidazo[1...
Compound Q&A
What is the market or research trend for N-Ethyl-3,4-dimethylbenzylamine (CAS: 39180-83-1)?
The market for N-Ethyl-3,4-dimethylbenzylamine (CAS: 39180-83-1) remains steady,...
39180-83-1N-Ethyl-3,4-dimethyl...
Compound Q&A
What is Tert-butyl 3-(pyrrolidin-1-yl)azetidine-1-carboxylate (CAS: 1019008-21-9)?
Tert-butyl 3-(pyrrolidin-1-yl)azetidine-1-carboxylate is a chemical compound wit...
1019008-21-9Tert-butyl 3-(pyrrol...
Compound Q&A
What regulatory guidelines apply to 1-Bromo-3-chloro-2,4-dimethoxybenzene (CAS: 1228956-93-1)?
1-Bromo-3-chloro-2,4-dimethoxybenzene (CAS: 1228956-93-1) falls under the classi...
1228956-93-11-Bromo-3-chloro-2,4...
Compound Q&A
Is 8-Bromo-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (CAS: 1368622-07-4) safe?
The safety of 8-Bromo-2-methyl-3,4-dihydroisoquinolin-1(2H)-one (CAS: 1368622-07...
1368622-07-48-Bromo-2-methyl-3,4...
Compound Q&A
Is Benzyl [(3S)-2,6-dioxo-3-piperidinyl]carbamate (CAS: 22785-43-9) safe?
Benzyl [(3S)-2,6-dioxo-3-piperidinyl]carbamate is generally safe when handled wi...
22785-43-9Benzyl [(3S)-2,6-dio...
Compound Q&A
How should 1-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]sulfonyl}pyrrolidine (CAS: 928657-21-0) be stored?
1-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]sulfonyl}pyrrolidine s...
928657-21-01-{[4-(4,4,5,5-Tetra...
Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
Methyl 2-amino-4-(4-chlorophenyl)-5-pyrimidinecarboxylate
CAS Number:
1133115-56-6
Molecular Formula:
C12H10ClN3O2
![(1R,6R)-6-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-cyclohexene-1-carboxylic acid structure](https://static.chemtradehub.com/structs/865/865689-24-3-5fef.webp "(1R,6R)-6-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-cyclohexene-1-carboxylic acid structure")
(1R,6R)-6-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-cyclohexene-1-carboxylic acid
CAS Number:
865689-24-3
Molecular Formula:
C12H19NO4
Recommended Suppliers
Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.