Pyridine-N-oxide catalyzed acylative desymmetrization of bisphenols: access to P-stereogenic phosphinates with low catalyst loadings

Literature Information

Publication Date 2023-10-31
DOI 10.1039/D3QO01499A
Impact Factor 5.281
Authors

Yang-Guang Chen, Ying Hu, Jia-Yi Liu, Ming-Sheng Xie


View Original

Abstract

A catalytic stereoselective strategy to access P-stereogenic phosphinates through chiral 4-arylpyridine-N-oxide-catalyzed acylative desymmetrization of bisphenols has been reported. In the presence of 0.05 mol% 4-arylpyridine-N-oxide catalyst, chiral P-stereogenic phosphinates were obtained in up to 97% yields and 96% ee under mild conditions for 2 h. A series of chiral phosphorus compounds containing carboxylic acid drug molecules such as gemfibrozil, isoxepac, and indomethacin were synthesized with high yields and high enantioselectivities.

Related Literature

Tuning photocatalytic performance of the near-infrared-driven photocatalyst Cu2(OH)PO4 based on effective mass and dipole moment

Zhujie Li, Ying Dai, Xiangchao Ma, Yingtao Zhu, Baibiao Huang

2013-11-11 Paper

DOI: 10.1039/C3CP53381F

Back cover

Cover

DOI: 10.1039/C4CP90007C

Dynamics and stability of lipid bilayers modulated by thermosensitive polypeptides, cholesterols, and PEGylated lipids

Hwankyu Lee, Hyun Ryoung Kim, Jae Chan Park

2013-12-17 Paper

DOI: 10.1039/C3CP52639A

Carbon-coated LiCrTiO4 electrode material promoting phase transition to reduce asymmetric polarization for lithium-ion batteries

Bo Yan, Jing Ye, Xue Li, Yansheng Liu, Haiping You

2013-11-19 Paper

DOI: 10.1039/C3CP54399D

Optimization of amorphous silicon double junction solar cells for an efficient photoelectrochemical water splitting device based on a bismuth vanadate photoanode

Lihao Han, Paula Perez Rodriguez, Bernard Dam, Miro Zeman, Arno H. M. Smets

2014-01-02 Paper

DOI: 10.1039/C3CP55035D

Determination of volatility of ionic liquids at the nanoscale by means of ultra-fast scanning calorimetry

Mathias Ahrenberg, Marcel Brinckmann, Jürn W. P. Schmelzer, Martin Beck, Christin Schmidt

2013-11-15 Paper

DOI: 10.1039/C3CP54325K

Electric quadrupole moment of graphene and its effect on intermolecular interactions

Mikuláš Kocman, Martin Pykal, Petr Jurečka

2013-12-06 Paper

DOI: 10.1039/C3CP54701A

Plasmon-enhanced water splitting on TiO2-passivated GaP photocatalysts

Jing Qiu, Guangtong Zeng, Prathamesh Pavaskar, Zhen Li

2013-12-20 Paper

DOI: 10.1039/C3CP54674H

A donor–acceptor pair for the real time study of vibrational energy transfer in proteins

Henrike M. Müller-Werkmeister, Jens Bredenbeck

2013-12-19 Paper

DOI: 10.1039/C3CP54760D

You might also like

Compound Q&A

What is the market or research trend for N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0)?

N-(4-Methoxybenzyl)-2-pyridinamine (CAS: 52818-63-0) is increasingly being used ...

52818-63-0N-(4-Methoxybenzyl)-...
Compound Q&A

What precautions should be taken when handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate (CAS: 1050507-06-6)?

When handling Ethyl 4-(2-chlorophenyl)-1,3-thiazole-2-carboxylate, appropriate p...

1050507-06-6Ethyl 4-(2-chlorophe...
Compound Q&A

What regulatory guidelines apply to diethyldiselane (CAS: 628-39-7)?

Diethyldiselane (CAS: 628-39-7) is classified under the Globally Harmonized Syst...

628-39-7Diethyldiselane
Compound Q&A

What is the market or research trend for oxocopper (CAS: 12053-18-8)?

The market for oxocopper (CAS: 12053-18-8) is primarily driven by its use in cat...

12053-18-8oxocopper; oxo-(oxoc...
Compound Q&A

What is the market or research trend for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-carboxylic acid?

The market for 5-{[(2-Methyl-2-propanyl)oxy]carbonyl}-5-azaspiro[2.4]heptane-7-c...

1268519-54-55-{[(2-Methyl-2-prop...
Compound Q&A

What is 2-(1-Pyrrolidinyl)-4-pyridinamine (CAS: 35981-63-6)?

2-(1-Pyrrolidinyl)-4-pyridinamine is a chemical compound with the CAS number 359...

35981-63-62-(1-Pyrrolidinyl)-4...
Compound Q&A

What are the physical and chemical properties of 2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1)?

2-(3-Pyridinyl)-1-azabicyclo[2.2.2]octane (CAS: 91556-75-1) is a crystalline sol...

91556-75-12-(3-Pyridinyl)-1-az...
Compound Q&A

How is (S)-Alpha-allyl-proline hydrochloride (CAS: 129704-91-2) typically synthesized?

(S)-Alpha-allyl-proline hydrochloride is usually synthesized via a Wittig reacti...

129704-91-2(S)-Alpha-allyl-prol...
Compound Q&A

What is 3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5)?

3-Methyl-1,2-oxazole-5-carboxylic acid (CAS: 4857-42-5) is an organic compound w...

4857-42-53-Methyl-1,2-oxazole...
Compound Q&A

How is Lys-SMCC-DM1 (CAS: 1281816-04-3) typically synthesized?

Lys-SMCC-DM1 is synthesized via a multi-step process involving the coupling of S...

1281816-04-3Lys-SMCC-DM1

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.