Sugar-based ethenyl ethers: stereoselective dipolar cycloadditions of nitrile oxides

Desroses, Matthieu; Chéry, Florence; Tatibouët, Arnaud; Lucchi, Ottorino De; Rollin, Patrick

doi:10.1016/s0957-4166(02)00709-7

Cited by 22 publications

(5 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Elemental analy sis was carried out on an automated Perkin-Elmer 2400 CHN microanalyzer. Etoxycarbonylformohydroximoyl chloride, 10 4 methoxybenzohydroximoyl chloride, 15 2,4,6 trimethylben zonitrile oxide, 16 isomyristicin, 17 isoapiol, 17 and isodillapiol 17 were synthesized according to known procedures.…”

Section: Methodsmentioning

confidence: 99%

Polyalkoxybenzenes from plant sources 2. Synthesis of isoxazoline analogs of combretastatin from natural allyl(methylenedioxy)methoxybenzenes

et al. 2007

View full text Add to dashboard Cite

A series of analogs of the natural mitostatic agent combretastatin were synthesized by the reaction of nitrile oxides with natural allylbenzenes, such as myristicin, apiol, and dillapiol. The 1,3 dipolar cycloaddition reactions in allylic systems proceed regiospecifically. The reac tions with trans isomers of propenylbenzenes, viz., isomyristicin, isoapiol, and isodillapiol, as dipolarophiles produce regioisomers.

show abstract

Section: Methodsmentioning

confidence: 99%

Polyalkoxybenzenes from plant sources 2. Synthesis of isoxazoline analogs of combretastatin from natural allyl(methylenedioxy)methoxybenzenes

et al. 2007

View full text Add to dashboard Cite

show abstract

“…The same year, some ROCH=CH 2 type vinyl ethers (R = sugar motif) were used as chiral templates responsible for asymmetric induction in the syntheses of substituted isoxazolines via 1,3-DP cycloaddition of nitrile oxides to ROvinyl— Scheme 18 [ 21 ].…”

Section: Syntheses Of Substituted 2-isoxazolines Via 13-dp Cycloaddit...mentioning

confidence: 99%

“… Asymmetric induction in the syntheses of 3,5-disubstituted isoxazolines: sugar motifs as chiral templates [ 21 ]. Ar = Ph, 2,4,6-trimethyl- and trimethoxyphenyl; a = pyridine + Et 3 N, Et 2 O + CHCl 3 , rfx, 2 h; up to 98% yield; epimeric ratio = from 1:1 to 28:1.…”

Section: Figures and Schemesmentioning

confidence: 99%

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

et al. 2023

View full text Add to dashboard Cite

The involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated nitrile oxide) as dipoles, together with the C=C bond containing dipolarophiles, in the syntheses of 2-isoxazolines is presented. Methods for synthesizing isoxazolines (other than 1,3-DP cycloaddition) were also presented briefly. Various methods of nitrile oxide preparation, especially in situ-generated procedures, are presented. Special attention was paid to the application of various combinations of 1,3-DP cycloaddition with double bond migration (DBM) and with alkene metathesis (AM) in the syntheses of trisubstituted isoxazolines. Allyl compounds of the type QCH2CH=CH2 (Q = ArO, ArS, Ar, and others) play the role of dipolarophile precursors in the combinations of DPC mentioned, DBM and AM. Mechanistic aspects of cycloadditions, i.e., concerted or stepwise reaction mechanism and their regio- and stereoselectivity are also discussed from experimental and theoretical points of view. Side reactions accompanying cycloaddition, especially nitrile oxide dimerization, are considered. 2-Isoxazoline applications in organic synthesis and their biological activity, broad utility in medicine, agriculture, and other fields were also raised. Some remaining challenges in the field of 1,3-DP cycloaddition in the syntheses of isoxazolines are finally discussed.

show abstract

“…Enol ethers derived from carbohydrates have been used for the synthesis of isoxazolines. Rollin et al [35] investigated the importance of proximity between the chiral template and the reacting group by investigating diastereomeric ratio (epimeric ratio) of isoxazolines obtained by reacting enol ethers derived from D-galactose 31a, D-fructose 31b, and D-psicose 31c with nitrile oxides. The reaction of enol ethers with aromatic nitrile oxides generated by dehydrohalogenation of hydroximoyl halides proceeded with moderate to good yields.…”

Section: Nitrile Oxide Cycloaddition Of Vinyl Ethers Enol Ethers Andmentioning

confidence: 99%

Recent Advances in Nitrile Oxide Cycloadditions. Synthesis of Isoxazolines

Sibi¹

2011

COS

View full text Add to dashboard Cite

Synthesis of novel heterocyclic compounds continues to be an important and challenging task. Isoxazolines are one such class of heterocyclic molecules of significance, since they are frequently found in many compounds that show significant biological activity. They are also of importance since they can be easily transformed into important functional groups. Nitrile oxide cycloaddition with carbon dipolarophiles represents an easy route to the synthesis of these molecules. Research groups over the past decades have established novel protocols and methods for the synthesis of isoxazolines via dipolar cycloaddition. This review will highlight the success that has been achieved in this field since 2000.

show abstract

Sugar-based ethenyl ethers: stereoselective dipolar cycloadditions of nitrile oxides

Cited by 22 publications

References 17 publications

Polyalkoxybenzenes from plant sources 2. Synthesis of isoxazoline analogs of combretastatin from natural allyl(methylenedioxy)methoxybenzenes

Polyalkoxybenzenes from plant sources 2. Synthesis of isoxazoline analogs of combretastatin from natural allyl(methylenedioxy)methoxybenzenes

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

Recent Advances in Nitrile Oxide Cycloadditions. Synthesis of Isoxazolines

Contact Info

Product

Resources

About