The Nitrile Oxide/Isoxazoline Route to C ‐Disaccharides

1997 ◽  
pp. 49-66
Author(s):  
R. M. Paton
Keyword(s):  
Nitrile Oxide

π-Facial Selectivity in 1,3-Dipolar Cycloaddition Reactions of α-Methylidene-γ-lactone Substituted by 4-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl Group in γ-Position

2002 ◽  
Vol 67 (3) ◽  
pp. 353-364 ◽  
Author(s):  
Petr Melša ◽  
Ctibor Mazal
Keyword(s):  
Double Bond ◽  
Carboxylic Acid ◽  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Enantiomerically Pure ◽  
Nitrile Imine ◽  
Facial Selectivity ◽  
Excellent Selectivity

Diastereoselectivity of 1,3-dipolar cycloaddition reactions of benzyl azide, diazomethane, a nitrile oxide and a nitrile imine to α-methylidene-γ-lactone dipolarophile was effectively controlled by a bulky γ-substituent, 4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl in γ-position of the dipolarophile. The dipoles added from the less hindered face of the double bond with an excellent selectivity. Enantiomerically pure dipolarophile was prepared from the easily available (S)-5-oxotetrahydrohydrofuran-2-carboxylic acid.

Hypervalent-Iodine Mediated One-Pot Synthesis of Isoxazolines and Isoxazoles bearing Difluoromethyl Phosphonate Moiety

2021 ◽  
Author(s):  
Romana Pajkert ◽  
Henryk Koroniak ◽  
Pawel Kafarski ◽  
Gerd Volker Roeschenthaler
Keyword(s):  
Nitrile Oxide ◽  
Dipolar Cycloaddition ◽  
Hypervalent Iodine ◽  
One Pot ◽  
One Pot Synthesis

A one-pot, regioselective 1,3-dipolar cycloaddition of in situ generated (diethoxyphosphoryl)difluoromethyl nitrile oxide toward selected alkenes and alkynes is reported. This protocol enables facile access to 3,5-disubstituted isoxazolines and isoxazoles bearing...

A Novel Nitrile Oxide Precursor; 2-Methyl-4-nitro-5(2H)-isoxazolone

Heterocycles ◽  
1992 ◽  
Vol 34 (8) ◽  
pp. 1511 ◽  
Author(s):  
Masahiro Ariga ◽  
Suguru Higashida ◽  
Hiroko Nakashima ◽  
Yasuo Tohda ◽  
Keita Tani ◽  
...  
Keyword(s):  
Nitrile Oxide ◽  
Oxide Precursor

Difluoromethyl Nitrile Oxide (CF2HCNO): A Neglected Chemical Reagent

2017 ◽  
Vol 2017 (27) ◽  
pp. 3935-3940 ◽  
Author(s):  
Andrii Khutorianskyi ◽  
Bohdan Chalyk ◽  
Petro Borysko ◽  
Anna Kondratiuk ◽  
Pavel K. Mykhailiuk
Keyword(s):  
Nitrile Oxide ◽  
Chemical Reagent

Chiral Lewis Acid Catalysis in Nitrile Oxide Cycloadditions

2004 ◽  
Vol 126 (17) ◽  
pp. 5366-5367 ◽  
Author(s):  
Mukund P. Sibi ◽  
Kennosuke Itoh ◽  
Craig P. Jasperse
Keyword(s):  
Lewis Acid ◽  
Acid Catalysis ◽  
Nitrile Oxide ◽  
Lewis Acid Catalysis ◽  
Chiral Lewis Acid

ChemInform Abstract: Nitrile Oxide-BF3 Complex as Electrophilic Moiety Towards Aromatic Systems: Stereospecific Synthesis of Oximes.

ChemInform ◽  
2010 ◽  
Vol 25 (48) ◽  
pp. no-no
Author(s):  
S. AURICCHIO ◽  
A. BINI ◽  
E. PASTORMERLO ◽  
A. RICCA ◽  
A. M. TRUSCELLO
Keyword(s):  
Nitrile Oxide ◽  
Stereospecific Synthesis ◽  
Aromatic Systems

ChemInform Abstract: Novel Trinitrogen-Containing Triheterocycles via the Intramolecular Nitrile Oxide Cycloaddition Reaction.

ChemInform ◽  
2012 ◽  
Vol 43 (9) ◽  
pp. no-no
Author(s):  
Andrew J. Ferreira ◽  
Danielle M. Solano ◽  
James S. Oakdale ◽  
Mark J. Kurth
Keyword(s):  
Cycloaddition Reaction ◽  
Nitrile Oxide

Diversity-Oriented Synthesis of Highly Functionalized Alicycles across Dipolar Cycloaddition/Metathesis Reaction

Synlett ◽  
2021 ◽  
Author(s):  
Loránd Kiss ◽  
Zsanett Benke ◽  
Melinda Nonn ◽  
Attila M. Remete ◽  
Santos Fustero
Keyword(s):  
Amino Acid ◽  
Ring Opening ◽  
Nitrile Oxide ◽  
Amino Acid Derivatives ◽  
Selective Synthesis ◽  
Chemical Transformations ◽  
Bond Functionalization ◽  
Cross Metathesis ◽  
Chlorosulfonyl Isocyanate ◽  
Biological Potential

AbstractThis Account gives an insight into the selective functionalization of some readily available commercial cyclodienes across simple chemical transformations into functionalized small-molecular scaffolds. The syntheses involved selective cycloadditions, followed by ring-opening metathesis (ROM) of the resulting azetidin-2-one derivatives or isoxazoline frameworks and selective cross metathesis (CM) by discrimination of the C=C bonds on the alkenylated heterocycles. The CM protocols have been described when investigated under various conditions with the purpose on exploring chemodifferentiation of the olefin bonds and a study on the access of the corresponding functionalized β-lactam or isoxazoline derivatives is presented. Due to the expanding importance of organofluorine chemistry in drug research as well as of the high biological potential of β-lactam derivatives several illustrative examples to the access of some fluorine-containing molecular entities is also presented in this synopsis.1 Introduction2 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Chlorosulfonyl Isocyanate Cycloaddition3 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Nitrile Oxide Cycloaddition4 Ring C=C Bond Functionalization of Some Cycloalkene β-Amino Acid Derivatives across Metathesis5 Functionalization of sSome Cyclodienes across Nitrile Oxide Cycloaddition6 Selective Synthesis of Functionalized Alicycles across Ring-Opening Metathesis7 Selective Synthesis of Functionalized Alicycles through Cross Metathesis8 Summary and Outlook9 List of Abbreviations

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