An Azophosphine Synthetic Equivalent of Mesitylphosphaazide and Its 1,3-Dipolar Cycloaddition Reactions

2021 ◽  
Author(s):  
Martin-Louis Y. Riu ◽  
Wesley J. Transue ◽  
Jan M. Rall ◽  
Christopher C. Cummins
Keyword(s):  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Synthetic Equivalent

1,3-Dipolar Cycloadditions Involving Allenes: Synthesis of Five-Membered Rings

2020 ◽  
Vol 23 (27) ◽  
pp. 3064-3134 ◽  
Author(s):  
Ana L. Cardoso ◽  
Maria I.L. Soares
Keyword(s):  
Transition Metal ◽  
Cycloaddition Reaction ◽  
Building Blocks ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Relevant Research ◽  
Dipolar Cycloadditions ◽  
Recent Developments ◽  
Synthetic Equivalent ◽  
Metal Catalyzed

The 1,3-dipolar cycloaddition reaction is a powerful and versatile strategy for the synthesis of carbocyclic and heterocyclic five-membered rings. Herein, the most recent developments on the [3+2] cycloaddition reactions using allenes acting either as dipolarophiles or 1,3-dipole precursors, are highlighted. The recent contributions on the phosphine- and transition metal-catalyzed [3+2] annulations involving allenes as substrates are also covered, with the exception of those in which the formation of a 1,3-dipole (or synthetic equivalent) is not invoked. This review summarizes the most relevant research in which allenes are used as building blocks for the construction of structurally diverse five-membered rings via [3+2] annulation 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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