Enolate-mediated 1,3-dipolar cycloaddition reaction of β-functionalized ketones with nitrile oxides: direct access to 3,4,5-trisubstituted isoxazoles

2016 ◽  
Vol 14 (23) ◽  
pp. 5246-5250 ◽  
Author(s):  
Xiao Zhou ◽  
Xianhong Xu ◽  
Zhenyan Shi ◽  
Kun Liu ◽  
Hua Gao ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Nitrile Oxides ◽  
High Yields

Enolate-mediated [3 + 2] organocatalytic 1,3-dipolar cycloaddition reactions of β-functionalized ketones with nitrile oxides have been developed. This strategy could generate 3,4,5-trisubstituted isoxazole in high yields and regioselectivities.

Direct access to 1,4-disubstituted 1,2,3-triazoles through organocatalytic 1,3-dipolar cycloaddition reaction of α,β-unsaturated esters with azides

RSC Advances ◽  
2015 ◽  
Vol 5 (108) ◽  
pp. 88816-88820 ◽  
Author(s):  
Wenjun Li ◽  
Xiao Zhou ◽  
Yepeng Luan ◽  
Jian Wang
Keyword(s):  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Unsaturated Esters ◽  
High Yields

DBU-catalyzed organocatalytic 1,3-dipolar cycloaddition reactions of α,β-unsaturated esters with azides have been developed. This strategy generates 1,4-disubstituted 1,2,3-triazoles in high yields with high regioselectivities.

Enolate-mediated 1,3-dipolar cycloaddition reactions of allyl ketones with nitrile oxides: direct access to 3,5-disubstituted isoxazolines

2016 ◽  
Vol 14 (42) ◽  
pp. 9985-9988 ◽  
Author(s):  
Wenjun Li ◽  
Xiao Zhou ◽  
Zhenyan Shi ◽  
Yang Liu ◽  
Zhantao Liu ◽  
...  
Keyword(s):  
Direct Access ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Nitrile Oxides ◽  
High Yields

TMG-catalyzed [3 + 2] organocatalytic 1,3-dipolar cycloaddition reactions of allyl ketones with in situ generated nitrile oxides have been developed. This strategy could generate 3,5-disubstituted isoxazolines in high yields and regioselectivities.

Spiroheterocycles via Regioselective Cycloaddition Reactions of Nitrile Oxides with 5-Methylene-1H-pyrrol-2(5H)-ones

2010 ◽  
Vol 63 (3) ◽  
pp. 445 ◽  
Author(s):  
Nicola J. Beattie ◽  
Craig L. Francis ◽  
Andris J. Liepa ◽  
G. Paul Savage
Keyword(s):  
Cycloaddition Reaction ◽  
Biphasic System ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Nitrile Oxides ◽  
Facial Selectivity

Substituted 5-methylene-1H-pyrrol-2(5H)-ones underwent a 1,3-dipolar cycloaddition reaction with nitrile oxides to give the corresponding spiro heterocycles. Critical to this reaction was the development of a biphasic system for base-induced dehydrohalogenation of hydroximoyl chlorides, to give nitrile oxides, in the presence of a base-sensitive dipolarophile. A substituted N-tolyl 5-methylene-1H-pyrrol-2(5H)-one exhibited atropisomerism, which in turn led to a 4:1 facial selectivity during cycloaddition.

Organocatalytic 1,3-dipolar [3+3] cycloaddition reaction of 1,2-cyclohexanedione with azides: direct access to highly substituted 1,2,3-triazoles

2016 ◽  
Vol 40 (8) ◽  
pp. 6559-6563 ◽  
Author(s):  
Xianhong Xu ◽  
Zhenyan Shi ◽  
Wenjun Li
Keyword(s):  
Cycloaddition Reaction ◽  
Direct Access ◽  
Cycloaddition Reactions ◽  
High Yields

Enamine-mediated 1,3-dipolar [3+3] cycloaddition reactions of 1,2-cyclohexanedione with azides have been developed. This strategy could generate highly substituted 1,2,3-triazoles in high yields and high levels of regioselectivities. It is demonstrated that various types of products could be obtained with different organocatalysts and substrates.

Direct access to isoxazolino and isoxazolo benzazepines from 2-((hydroxyimino)methyl)benzoic acid via a post-Ugi heteroannulation

2017 ◽  
Vol 15 (27) ◽  
pp. 5737-5742 ◽  
Author(s):  
Saeed Balalaie ◽  
Mohammad Shamakli ◽  
Ali Nikbakht ◽  
Nahid S. Alavijeh ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Benzoic Acid ◽  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition ◽  
Nitrile Oxides

A diversity-oriented access to isoxazolino and isoxazolo benzazepines is elaborated via a post-Ugi heteroannulation involving intramolecular 1,3-dipolar cycloaddition reaction of nitrile oxides with alkenes and alkynes.

A NHC-catalyzed 1,3-dipolar cycloaddition reaction of allyl ketones with azides: direct access to 1,4,5-trisubstituted 1,2,3-triazoles

2017 ◽  
Vol 15 (20) ◽  
pp. 4286-4290 ◽  
Author(s):  
Huijun Yuan ◽  
Lili Zhang ◽  
Zhantao Liu ◽  
Yang Liu ◽  
Jian Wang ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Direct Access ◽  
Dipolar Cycloaddition ◽  
High Yields

A NHC-catalyzed 1,3-dipolar cycloaddition reaction of allyl ketones with azides has been developed. This strategy could generate 1,4,5-trisubstituted 1,2,3-triazoles in high yields and regioselectivities in the presence of a 20 mol% N-heterocyclic carbene catalyst. A broad substrate scope of this process is also presented.

Regio- and diastereo-selective formation of Isoxazoline Derivatives by Lewis acid Mediated 1,3-dipolar Cycloaddition Reactions of Nitrile Oxide

2007 ◽  
Vol 2007 (7) ◽  
pp. 394-396 ◽  
Author(s):  
Saori Hayashi ◽  
Akira Mori ◽  
Masatoshi Nishina ◽  
Masanori Sumimoto ◽  
Kenzi Hori ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Cycloaddition Reaction ◽  
Chiral Auxiliary ◽  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Magnesium Perchlorate ◽  
Nitrile Oxides ◽  
Selective Formation

In the presence of magnesium perchlorate, 1,3-dipolar cycloaddition reactions of nitrile oxides to crotonamide bearing 4-benzyl-5,5-dimethyl-1,3-oxazolidin-2-one as the chiral auxiliary proceeded with a regio- and diastereo-selective manner to afford the corresponding chiral 2-isoxazoline. The mechanisms underlying the diastereoface selection in the cycloaddition reaction were investigated using the B3LYP/6-31G* level of theory.

1,3-Dipolar cycloaddition reactions of nitrile oxides in the synthesis of natural compounds and their analogues

2001 ◽  
Vol 70 (8) ◽  
pp. 641-653 ◽  
Author(s):  
Anna I Kotyatkina ◽  
Vladimir N Zhabinsky ◽  
Vladimir A Khripach
Keyword(s):  
Natural Compounds ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Nitrile Oxides
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