ChemInform Abstract: Synthesis and Structure of Condensed Heterocycles Derived from Intramolecular 1,3-Dipolar Cycloaddition of Transient and Enantiomerically Pure α-Allylamino Nitrones and Nitrile Oxides in a High Level of Diastereoselectivity.

ChemInform ◽  
2010 ◽  
Vol 31 (25) ◽  
pp. no-no
Author(s):  
Md. Jashim Uddin ◽  
Minoru Kikuchi ◽  
Ken Takedatsu ◽  
Ken-Ichi Arai ◽  
Tetsuya Fujimoto ◽  
...  
Keyword(s):  
Dipolar Cycloaddition ◽  
Enantiomerically Pure ◽  
Nitrile Oxides ◽  
High Level ◽  
Condensed Heterocycles

scholarly journals Synthesis of novel spiro-isoxazoline and spiro-isoxazolidine derivatives of tomentosin

RSC Advances ◽  
2017 ◽  
Vol 7 (11) ◽  
pp. 6523-6529 ◽  
Author(s):  
Mohamed Zaki ◽  
Abdelouahd Oukhrib ◽  
Mohamed Akssira ◽  
Sabine Berteina-Raboin
Keyword(s):  
Double Bond ◽  
Dipolar Cycloaddition ◽  
Exocyclic Double Bond ◽  
Enantiomerically Pure ◽  
Nitrile Oxides ◽  
Dittrichia Viscosa ◽  
Derivatives Of

A series of novel enantiomerically pure spiro-(isoxazolidines/isoxazolines) were synthesized regioselectively by 1,3-dipolar cycloaddition using nitrones and nitrile oxides, on the exocyclic double bond of tomentosin extracted from Dittrichia viscosa.

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.

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