ChemInform Abstract: Highly Regioselective Dipolar Cycloadditions of Nitrile Oxides with α,β-Acetylenic Aldehydes.

ChemInform ◽  
2016 ◽  
Vol 47 (23) ◽  
Author(s):  
Longqiang Jiang ◽  
Tao Gao ◽  
Zhi Li ◽  
Shaofa Sun ◽  
Claudia Kim ◽  
...  
Keyword(s):  
Dipolar Cycloadditions ◽  
Nitrile Oxides

1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with nitrile oxides and nitrones

Tetrahedron ◽  
2010 ◽  
Vol 66 (25) ◽  
pp. 4564-4572 ◽  
Author(s):  
Marie Kissane ◽  
Simon E. Lawrence ◽  
Anita R. Maguire
Keyword(s):  
Dipolar Cycloadditions ◽  
Nitrile Oxides

Stereoconvergent and stepwise 1,3-dipolar cycloadditions of nitrile oxides and nitrile imines

2021 ◽  
Author(s):  
Zhenni Zhao ◽  
Zhi Ou ◽  
Subarna Jyoti Kalita ◽  
Feng Cheng ◽  
Qian Huang ◽  
...  
Keyword(s):  
Dipolar Cycloadditions ◽  
Nitrile Oxides ◽  
Nitrile Imines

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.

1,3-Dipolar Cycloadditions of a Chiral Oxazolidinone With Nitrones and Nitrile Oxides

1995 ◽  
Vol 48 (9) ◽  
pp. 1511 ◽  
Author(s):  
SG Pyne ◽  
J Safaei-G ◽  
BW Skelton ◽  
AH White
Keyword(s):  
Single Crystal ◽  
Hydrogen Atmosphere ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
The Novel ◽  
X Ray ◽  
Dipolar Cycloadditions ◽  
Nitrile Oxides ◽  
Exocyclic Methylene

The 1,3-dipolar cycloaddition reactions of the chiral oxazolidinone (1) and nitrones are highly regioselective and only 5,5-disubstituted isoxazolidine adducts are formed. These reactions occur under equilibrating conditions to give the more stable adducts that result from addition to the exocyclic methylene of (1) from the sterically more hindered π-face. The endo adducts are generally thermodynamically favoured. In one case the novel azetidine (21) was formed from the treatment of the adduct (4a) with palladium hydroxide on carbon under a hydrogen atmosphere. The major adducts from the reaction of (1) and nitrile oxides (16a,b) had the expected stereochemistry, addition of the 1,3-dipole having occurred from the less hindered π-face of the exocyclic methylene of (1). The stereochemistry of many of these products has been elucidated by single-crystal X-ray structural determinations.

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