scholarly journals Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction

2014 ◽  
Vol 10 ◽  
pp. 2892-2896 ◽  
Author(s):  
Chun-Huan Jiang ◽  
Xiantao Lei ◽  
Le Zhen ◽  
Hong-Jin Du ◽  
Xiaoan Wen ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Reducing Power ◽  
Isomerization Reaction ◽  
Hydride Shift ◽  
Acid Catalyzed ◽  
High Yields

Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolcular [1,5]-hydride shift/isomerization reaction has been realized, using the inherent reducing power of 3-pyrrolines. A series of N-arylpyrrole containing amines are obtained in high yields.

Efficient Synthesis of Diarylmethylamines via Lewis Acid Catalyzed Friedel–Crafts Reactions of Donor–Acceptor Aziridines with N,N-Dialkylanilines

Synthesis ◽  
2019 ◽  
Vol 52 (02) ◽  
pp. 281-289
Author(s):  
Yerin Kim ◽  
Yong Il Kwon ◽  
Sung-Gon Kim
Keyword(s):  
Lewis Acid ◽  
Efficient Synthesis ◽  
Broad Scope ◽  
Donor Acceptor ◽  
Acid Catalyzed ◽  
High Yields

A method for efficient and mild synthesis of diarylmethylamine scaffold, via Lewis acid catalyzed Friedel–Crafts reaction of donor­–acceptor aziridines with N,N-dialkylanilines to afford a biologically important diarylmethylamine derivatives in high yields (up to 88%), is presented. This reaction is suitable for the synthesis of various diarylmethylamine derivatives and has a broad scope for electron-rich arenes, including dimethoxybenzene.

Lewis Acid-Catalyzed Rearrangement of Fluoroalkylated Propargylic Alcohols: An Alternative Approach to β-Fluoroalkyl-α,β-enones

Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 356-360 ◽  
Author(s):  
Manickavasakam Ramasamy ◽  
Hui-Chang Lin ◽  
Sheng-Chu Kuo ◽  
Min-Tsang Hsieh
Keyword(s):  
Lewis Acid ◽  
Propargylic Alcohols ◽  
Alternative Approach ◽  
Acid Catalyzed ◽  
High Yields ◽  
High Stereoselectivity

A practical Lewis acid-catalyzed Meyer–Schuster rearrangement of fluoroalkylated propargylic alcohols, leading to a series of β-fluoroalkyl-α,β-enones, is developed. The methodology reported herein features moderate to high yields and high stereoselectivity in the synthesis of β-alkyl-β-fluoroalkyl-α,β-enones.

Facile Synthesis of Oxime Amino Ethers via Lewis Acid Catalyzed SN2-Type Ring Opening of Activated Aziridines with Aryl Aldehyde Oximes

Synlett ◽  
2020 ◽  
Vol 31 (07) ◽  
pp. 708-712
Author(s):  
Aditya Bhattacharyya ◽  
Subhomoy Das ◽  
Navya Chauhan ◽  
Pronay K. Biswas ◽  
Manas K. Ghorai
Keyword(s):  
Lewis Acid ◽  
Ring Opening ◽  
Facile Synthesis ◽  
Simple Strategy ◽  
Wide Range ◽  
Aryl Aldehyde ◽  
Acid Catalyzed ◽  
High Yields

A simple strategy to access a wide range of substituted oxime amino ethers in good to high yields via Lewis acid catalyzed SN2-type ring opening of activated aziridines with aryl aldehyde oximes is reported.

ChemInform Abstract: Construction of Oxadiazepines via Lewis Acid-Catalyzed Tandem 1,5-Hydride Shift/Cyclization.

ChemInform ◽  
2016 ◽  
Vol 47 (9) ◽  
pp. no-no
Author(s):  
Yong-Zhi Chang ◽  
Ming-Lei Li ◽  
Wen-Feng Zhao ◽  
Xiaoan Wen ◽  
Hongbin Sun ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Hydride Shift ◽  
Acid Catalyzed

Construction of Oxadiazepines via Lewis Acid-Catalyzed Tandem 1,5-Hydride Shift/Cyclization

2015 ◽  
Vol 80 (19) ◽  
pp. 9620-9627 ◽  
Author(s):  
Yong-Zhi Chang ◽  
Ming-Lei Li ◽  
Wen-Feng Zhao ◽  
Xiaoan Wen ◽  
Hongbin Sun ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Hydride Shift ◽  
Acid Catalyzed

Stereoselective synthesis of 3-spiropiperidino indoleninesviaSN2-type ring opening of activated aziridines with 1H-indoles/Pd-catalyzed spirocyclization with propargyl carbonates

2018 ◽  
Vol 54 (62) ◽  
pp. 8583-8586 ◽  
Author(s):  
Sajan Pradhan ◽  
Chandan Kumar Shahi ◽  
Aditya Bhattacharyya ◽  
Manas K. Ghorai
Keyword(s):  
Lewis Acid ◽  
Ring Opening ◽  
Stereoselective Synthesis ◽  
Synthetic Route ◽  
Acid Catalyzed ◽  
High Yields

A novel synthetic route to 3-spiropiperidino indoleninesviaLewis acid catalyzed SN2-type ring opening of activated aziridines with 1H-indoles followed by Pd-catalyzed spirocyclization with propargyl carbonates in high yields (up to 88%) with excellent diastereo- and enantiospecificity (dr >99 : 1; ee up to >99) is reported.

Synthesis of glycan fragments of glycoproteins using peracetylated N-allyloxycarbonyl-β-D-glucosamine and 1,6-anhydro-β-D-mannopyranose derivatives

1990 ◽  
Vol 68 (6) ◽  
pp. 828-835 ◽  
Author(s):  
Dominique Lafont ◽  
Paul Boullanger ◽  
Joseph Banoub ◽  
Gerard Descotes
Keyword(s):  
Lewis Acid ◽  
Free Amino ◽  
Acid Catalyzed ◽  
High Yields

The disaccharides β-D-GlcNAOC-(1 → 2)-D-Man, β-D-GlcNAOC-(1→ 4)-D-Man, the trisaccharide β-D-GlcNAOC-(1 → 2)-[β-D-GlcNAOC-(1→ 4)]-D-Man, and the tetrasaccharide β-D-GlcNAOC-(1 → 2)-[β-D-GlcNAOC-(1→ 3)]-[β-D-GlcNAOC-(1 → 4)]-D-Man have been synthesized in their peracetylated form, using the Lewis acid catalyzed condensations of 1,3,4,6-tetra-O-acetyl-2-N-allyloxycarbonylamino-2-deoxy-β-D-glucopyranose 1 with properly substituted 1,6-anhydro-β-D-mannopyranose derivatives. The anhydro glycosylation products obtained were then easily transformed into the 4C1 peracetylated derivatives by acetolysis. The N-allyloxycarbonyl groups could be converted into N-acetyl groups in the presence of Pd(0) complexes, followed by reacetylation of the free amino function in high yields. Keywords: N-allyloxycarbonyl, glycosylation, glucosamine, glycan fragments.

Highly diastereoselective access to polyfunctionalized 1,3-oxazines promoted by Brønsted/Lewis acids

2018 ◽  
Vol 5 (4) ◽  
pp. 566-570 ◽  
Author(s):  
Clovis Peter ◽  
Philippe Geoffroy ◽  
Michel Miesch
Keyword(s):  
Lewis Acid ◽  
Lewis Acids ◽  
Unsaturated Ketones ◽  
Acid Catalyzed ◽  
High Yields

The Brønsted/Lewis acid catalyzed reaction of α-alkyloxyamides tethered to α,β-unsaturated ketones (aldehydes) afforded exclusively polyfunctionalized 1,3-oxazines with high diastereoselectivities and in high yields.

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