Gold-catalysed synthesis of phosphonate-substituted oxetan-3-ones – an easy access to highly strained HWE reagents

Literature Information

Publication Date 2021-11-12
DOI 10.1039/D1QO01214B
Impact Factor 5.281
Authors

Shaista Tahir, Jonas F. Wunsch, Matthias Rudolph, Frank Rominger


View Original

Abstract

A convenient approach for the attainment of strained phosphonate-substituted oxetan-3-ones, starting from easy to synthesise alkynyl phosphonates, is presented. With the aid of a pyridine-N-oxide, in a gold-catalysed step an α-oxo carbene species is generated as a key intermediate. After formal OH-insertion, synthetically useful HWE reagents can be attained. The synthetic utility of the obtained building blocks could be demonstrated, which yielded the 2-alkenyl oxetan-3-one scaffold in high yields after the HWE reaction.

Related Literature

A novel shape-stabilized phase change material with tunable thermal conductivity for cold chain applications

Apoorv Balwani, Tridib Ambardar, Adarsh Kumar Pandey, Aravind Dasari, Sujay Chattopadhyay

2023-10-16 Paper

DOI: 10.1039/D3SU00289F

Eco-design of the remembrance poppy: a life cycle assessment study

Andrea Paulillo, Martina Pucciarelli, Phil Prior, Paola Lettieri

2023-11-28 Paper

DOI: 10.1039/D3SU00279A

Inside front cover

2024-01-03 Cover

DOI: 10.1039/D4SU90002B

Dye adsorption-assisted colloidal dispersion of single-walled carbon nanotubes in polar solvents

Akiho Horibe, Tomoko Murayama, Tsuyoshi Kawai, Yoshiyuki Nonoguchi

2023-09-18 Paper

DOI: 10.1039/D3LF00119A

Contents list

2024-01-25 Front/Back Matter

DOI: 10.1039/D4FB90002B

Sustainability-driven photocatalysis: oxygen-doped g-C3N4 for organic contaminant degradation

Soumya Ranjan Mishra, Vishal Gadore, Md. Ahmaruzzaman

2023-12-04 Tutorial Review

DOI: 10.1039/D3SU00384A

Towards sustainable synthesis: a life cycle assessment of polymer of intrinsic microporosity (PIM-1) by green mechanosynthesis

Ching Yoong Loh, Rui Huang, Roy Bell, Ming Xie

2023-10-26 Paper

DOI: 10.1039/D3SU00340J

Front cover

2023-11-16 Cover

DOI: 10.1039/D3FB90018E

Optimization of Pavlova gyrans biomass production and the fatty acid profile using a two-step approach

Filipe Maciel, Hugo Pereira, Joana Silva

2023-09-25 Paper

DOI: 10.1039/D3FB00110E

Construction of Pd–TiOx interfaces for selective hydrodeoxygenation of CO bonds in vanillin by supporting Pd nanoparticles on ETS-10 zeolite

Jianbin Huang, Chang Zhou, Jian Zhang, Hao Meng, Shiyao Lu

2023-11-14 Paper

DOI: 10.1039/D3SU00271C

You might also like

Compound Q&A

What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?

(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...

16326-97-9(1R,3S)-1,3-Cyclopen...
Compound Q&A

What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?

When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...

637-31-0N'-[4-(Dimethylamino...
Compound Q&A

Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?

There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...

1352318-16-15-(2,4-Difluoropheny...
Compound Q&A

What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?

1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...

382141-68-61-(3-Methoxyphenoxy)...
Compound Q&A

Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?

Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...

18660-81-6Tetrodotoxin Citrate
Compound Q&A

What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?

2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...

225641-84-92-Methyl-2-propanyl ...
Compound Q&A

How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?

Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...

16261-80-64-(2-Hydroxyhexafluo...
Compound Q&A

How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?

2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...

102507-19-72-Methyl-2-propanyl ...
Compound Q&A

What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?

Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...

20735-15-3Benzeneethanamine, α...
Compound Q&A

Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?

In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...

20691-84-33-{(E)-[4-(Dimethyla...

Source Journal

Organic Chemistry Frontiers

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

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.