scholarly journals Revealing Stepwise Mechanisms in Dipolar Cycloaddition Reactions: Computational Study of the Reaction between Nitrones and Isocyanates

2015 ◽  
Vol 81 (2) ◽  
pp. 673-680 ◽  
Author(s):  
Andrea Darù ◽  
David Roca-López ◽  
Tomás Tejero ◽  
Pedro Merino
Keyword(s):  
Computational Study ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions

Multicomponent 1,3-Dipolar Cycloaddition Reactions in the Construction of Hybrid Spiroheterocycles

2013 ◽  
Vol 17 (18) ◽  
pp. 1929-1956 ◽  
Author(s):  
Natarajan Arumugam ◽  
Raju Kumar ◽  
Abdulrahman Almansour ◽  
Subbu Perumal
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions

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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