Remarkably Selective Reduction of the α,β-Carbon—Carbon Double Bond in Highly Activated α,β,γ,δ-Unsaturated Alkenes by the InCl3—NaBH4 Reagent System.

ChemInform ◽  
2004 ◽  
Vol 35 (4) ◽  
Author(s):  
Brindaban C. Ranu ◽  
Sampak Samanta
Keyword(s):  
Double Bond ◽  
Selective Reduction ◽  
Carbon Double Bond

New agents for the selective reduction of the carbon-carbon double bond of .alpha.,.beta.-unsaturated carbonyl compounds

1991 ◽  
Vol 56 (23) ◽  
pp. 6720-6722 ◽  
Author(s):  
Yutaka Nishiyama ◽  
Masanori Yoshida ◽  
Shigeo Ohkawa ◽  
Sawako Hamanaka
Keyword(s):  
Double Bond ◽  
Carbonyl Compounds ◽  
Selective Reduction ◽  
New Agents ◽  
Carbon Double Bond ◽  
Alpha Beta

Reactions of 4-Pyrones with Azomethine Ylides as a Chemo­selective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines

Synthesis ◽  
2021 ◽  
Author(s):  
Dmitrii L. Obydennov ◽  
Vyacheslav D. Steben’kov ◽  
Konstantin L. Obydennov ◽  
Sergey A. Usachev ◽  
Vladimir S. Moshkin ◽  
...  
Keyword(s):  
Double Bond ◽  
Ring Opening ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Computational Studies ◽  
Carbon Double Bond ◽  
Reactivity Indexes ◽  
Reaction Proceeds

Abstract4-Pyrones bearing electron-donating and electron-withdrawing groups react with nonstabilized azomethine ylides to form pyrano[2,3-c]pyrrolidines in moderate to good yields. The reaction proceeds chemoselectively as a 1,3-dipolar cycloaddition of the azomethine ylide at the carbon–carbon double bond of the pyrone activated by the electron-withdrawing substituent. The reactivity of 4-pyrones toward azomethine ylides was rationalized by computational studies with the use of reactivity indexes. The pyrano[2,3-c]pyrrolidine moiety could be modified, for example by a ring-opening transformation under the action of hydrazine to provide pyrazolyl-substituted pyrrolidines.

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