scholarly journals C–H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds

2015 ◽  
Vol 51 (53) ◽  
pp. 10648-10651 ◽  
Author(s):  
YoungKu Kang ◽  
Matthew T. Richers ◽  
Conrad H. Sawicki ◽  
Daniel Seidel
Keyword(s):  
Carboxylic Acid ◽  
Carbonyl Compounds ◽  
Azomethine Ylides ◽  
Unsaturated Ketones ◽  
Cyclic Amines

Pyrrolidine and related amines undergo carboxylic acid promoted redox-annulations with α,β-unsaturated ketonesviathe intermediacy of conjugated azomethine ylides.

Divergent Functionalization of α,β-Enones: Catalyst-free Access to β-Azido Ketones and β-Amino α-Diazo Ketones

2021 ◽  
Author(s):  
Youshao Tu ◽  
honglin Dong ◽  
Huamin Wang ◽  
Yuhui Ao ◽  
Yu Liu
Keyword(s):  
Carbonyl Compounds ◽  
Practical Method ◽  
Free Access ◽  
Unsaturated Ketones ◽  
Catalyst Free

A simple and practical method for the azidation of β-fluoroalkyl α,β-unsaturated ketones to access a wide variety of fluorinated nitrogenous carbonyl compounds is developed. Different from existing precedents, neither metallic...

IBX as a catalyst for dehydration of hydroperoxides: green entry to α,β-unsaturated ketones via oxygenative allylic transposition

2018 ◽  
Vol 54 (7) ◽  
pp. 798-801 ◽  
Author(s):  
Tetsuya Kuga ◽  
Yusuke Sasano ◽  
Yoshiharu Iwabuchi
Keyword(s):  
Carbonyl Compounds ◽  
Catalytic Transformation ◽  
Unsaturated Ketones

A catalytic transformation of allylic hydroperoxides into α,β-unsaturated carbonyl compounds using IBX as a dehydration catalyst is described.

scholarly journals 3-Arylaziridine-2-carboxylic Acid Derivatives and (3-Arylaziridin-2-yl)ketones: The Aziridination Approaches

2021 ◽  
Vol 22 (18) ◽  
pp. 9861
Author(s):  
Boriss Strumfs ◽  
Romans Uljanovs ◽  
Kirils Velikijs ◽  
Peteris Trapencieris ◽  
Ilze Strumfa
Keyword(s):  
Carboxylic Acid ◽  
Carbonyl Compounds ◽  
Synthetic Chemistry ◽  
Significant Progress ◽  
Current Review ◽  
Recent Advances ◽  
Year 2000

Aziridination reactions represent a powerful tool in aziridine synthesis. Significant progress has been achieved in this field in the last decades, whereas highly functionalized aziridines including 3-arylated aziridine-2-carbonyl compounds play an important role in both medical and synthetic chemistry. For the reasons listed, in the current review we have focused on the ways to obtain 3-arylated aziridines and on the recent advances (mainly since the year 2000) in the methodology of the synthesis of these compounds via aziridination.

The 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides in Water Media

2021 ◽  
Vol 25 ◽  
Author(s):  
Joaquín Plumet
Keyword(s):  
Carbonyl Compounds ◽  
Critical Discussion ◽  
Aldol Reactions ◽  
Dipolar Cycloaddition ◽  
Hydroxy Ketone ◽  
Unsaturated Ketones ◽  
Dipolar Cycloadditions ◽  
Nitrile Oxides ◽  
Water Media ◽  
Synthetic Intermediates

: The 1,3-dipolar cycloadditions (DCs) of nitrile oxides (NOs) have been used as a powerful tool in synthetic organic chemistry. The cycloadducts arising from cycloadditions (CAs) of NOs to alkenes and alkynes (2-isoxazolines and isoxazoles respectively) are valuable synthetic intermediates because, among others, their capacity to mask other functionalities including α, β-unsaturated ketones, β-hydroxy carbonyl compounds and 1,3-aminoalcohols. In particular, the β-hydroxy ketone functionality is an illustrative example, making the NOs alkenes CAs reactions a synthetically equivalent methodology of aldol reactions. The vast majority of these reactions are carried out in organic solvents. Nevertheless, the use of water as an alternative solvent has evident advantages on the “Green Chemistry” concept. The critical discussion on the use of water instead of “conventional” solvents in the 1,3-DCs reactions of NOs is the objective of the present review.

Decarboxylative-Mediated Regioselective 1,3-Dipolar Cycloaddition for Diversity-Oriented Synthesis of Structurally exo′-Selective Spiro[oxindole-pyrrolidine-dihydrocoumarin] Hybrids

Synthesis ◽  
2020 ◽  
Author(s):  
Ying Zhou ◽  
Xiong-Wei Liu ◽  
Shun-Qin Chang ◽  
Qi-Lin Wang ◽  
Shuang Chen ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Transition State ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Diversity Oriented Synthesis ◽  
Biologically Relevant ◽  
Good Substrate ◽  
Quaternary Center ◽  
Substrate Tolerance ◽  
High Yields

A general and practical three-component regioselective 1,3-dipolar cycloaddition of 3-amino-oxindole-based azomethine ylides and coumarins has been developed. This reaction displayed good substrate tolerance and gave a diverse array of biologically relevant spiro[ox-­i­ndole-pyrrolidine-dihydrocoumarin] derivatives bearing four contiguous stereocenters including one spiro quaternary center in moderate to high yields (up to 90%) with high diastereoselectivities (up to 15:1 dr). It is based on the application of carboxylic acid activated coumarins as dienophiles followed by a decarboxylation process. The possible mechanism of the 1,3-dipolar cycloaddition is proposed via an exo′-transition state. Furthermore, this is the first example of decarboxylative-mediated regioselective 1,3-dipolar cycloaddition of 3-amino-oxindole-based azomethine ylides and coumarins.

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