Stereoselective synthesis of Δ(1)-pyrroline sulfonamides via a chiral aldehyde mediated cascade reaction
Literature Information
Publication Date
2023-11-15
DOI
10.1039/D3QO01675G
Impact Factor
5.281
Authors
Wei Wen, Zhao-Pin Ai, Zhu-Lian Wu, Tian Cai, Qi-Xiang Guo
View Original
Abstract
Functionalized chiral heterocycles play important roles in drug discovery and development. Cascade reactions are powerful strategies for the construction of structurally complex chiral heterocycles. Herein, a catalytic asymmetric Michael addition/spiroannulation/ring cleavage cascade reaction between NH2-free glycinate and cyclic 1-azadienes is established by using a novel chiral aldehyde catalyst, which results in the formation of optically active Δ(1)-pyrroline sulfonamides with high efficiency and high diastereo- and enantioselectivities. Notably, the use of the newly developed chiral aldehyde catalyst led to not only an enhanced reaction rate but also reversed chiral induction compared with its analogue bearing the same configurations.
Related Literature
Facile fabrication of robust superhydrophobic multilayered film based on bioinspired poly(dopamine)-modified carbon nanotubes
Jin-lei Wang, Ke-feng Ren, Hao Chang, Shi-miao Zhang, Lie-jiang Jin, Jian Ji
2013-12-02
Paper
DOI: 10.1039/C3CP54354D
Reactions of HOCO radicals through hydrogen-atom hopping utilizing clathrate hydrates as an observational matrix
Motoi Oshima, Atsushi Tani, Takeshi Sugahara, Katsuhisa Kitano, Kazunari Ohgaki
2013-12-18
Paper
DOI: 10.1039/C3CP54680B
Folding and unfolding thermodynamics of the TC10b Trp-cage miniprotein
Charles A. English, Angel E. García
2013-12-17
Perspective
DOI: 10.1039/C3CP54339K
Competitive pi interactions and hydrogen bonding within imidazolium ionic liquids
Richard P. Matthews, Tom Welton, Patricia A. Hunt
2014-01-09
Paper
DOI: 10.1039/C3CP54672A
Adsorption studies of a phosphonic acid on ITO: film coverage, purity, and induced electronic structure changes
S. A. Paniagua, E. L. Li, S. R. Marder
2013-12-19
Paper
DOI: 10.1039/C3CP54637C
Photoelectrochemical scanning droplet cell microscopy for localized photovoltaic investigations on organic semiconductors
Jacek Gasiorowski, Jan Philipp Kollender, Kurt Hingerl, Niyazi Serdar Sariciftci, Andrei Ionut Mardare
2013-11-18
Paper
DOI: 10.1039/C3CP53851F
Effects of process parameters on the defects in graphene oxide–polyaniline composites investigated by positron annihilation spectroscopy
Utpal Rana, P. M. G. Nambissan, Sudip Malik, Kuntal Chakrabarti
2013-12-16
Paper
DOI: 10.1039/C3CP54032D
The strong catalytic effect of Pb(ii) on the oxygen reduction reaction on 5 nm gold nanoparticles
Ying Wang, Blake J. Plowman, Kristina Tschulik, Kristopher R. Ward, Robert G. Palgrave, Christine Damm, Richard G. Compton
2013-12-20
Paper
DOI: 10.1039/C3CP55306J
The relationship between enhanced enzyme activity and structural dynamics in ionic liquids: a combined computational and experimental study
Sung Ho Ha, Latsavongsakda Sethaphong, Yoon-Mo Koo, Yaroslava G. Yingling
2013-12-02
Paper
DOI: 10.1039/C3CP52516C
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
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
![N-{[(2-Methyl-2-propanyl)oxy]carbonyl}-L-methionylglycine structure](https://static.chemtradehub.com/structs/234/23446-03-9-e1e5.webp "N-{[(2-Methyl-2-propanyl)oxy]carbonyl}-L-methionylglycine structure")
N-{[(2-Methyl-2-propanyl)oxy]carbonyl}-L-methionylglycine
CAS Number:
23446-03-9
Molecular Formula:
C12H22N2O5S
![1,10-bis(3,5-dimethylphenyl)-12-hydroxy-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocine 12-oxide structure](https://static.chemtradehub.com/structs/141/1412439-82-7-b9a9.webp "1,10-bis(3,5-dimethylphenyl)-12-hydroxy-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocine 12-oxide structure")
1,10-bis(3,5-dimethylphenyl)-12-hydroxy-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocine 12-oxide
CAS Number:
1412439-82-7
Molecular Formula:
C33H31O4P
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.