Nucleophilic Reactivity of the Carbon-Carbon Double Bond. IV.1The Effect of Chain Elongation. 3-(Δ3-Cyclopentenyl- and 3,4-dimethyl-Δ3-cyclopentenyl)-propyl p-Nitrobenzenesulfonates

1965 ◽  
Vol 87 (6) ◽  
pp. 1314-1319 ◽  
Author(s):  
Paul D. Bartlett ◽  
Walter S. Trahanovsky ◽  
Donald A. Bolon ◽  
George H. Schmid
Keyword(s):  
Double Bond ◽  
Chain Elongation ◽  
Carbon Double Bond ◽  
Nucleophilic Reactivity

Nucleophilic reactivity of the carbon-carbon double bond—V

Tetrahedron ◽  
1966 ◽  
Vol 22 ◽  
pp. 399-420 ◽  
Author(s):  
P.D. Bartlett ◽  
E.M. Nicholson ◽  
R. Owyang
Keyword(s):  
Double Bond ◽  
Carbon Double Bond ◽  
Nucleophilic Reactivity

Nucleophilic reactivity of the carbon-carbon double bond. VI. The use of urea as a base in acetolysis reactions

1967 ◽  
Vol 32 (1) ◽  
pp. 150-153 ◽  
Author(s):  
Walter S. Trahanovsky ◽  
Michael P. Doyle ◽  
Paul Doughty Bartlett
Keyword(s):  
Double Bond ◽  
Carbon Double Bond ◽  
Nucleophilic Reactivity

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.

scholarly journals Synthesis of (+)-solenopsin via Pd-catalyzed N-alkylation and cyclization

2021 ◽  
Vol 85 (2) ◽  
pp. 223-227
Author(s):  
Kana Suzuki ◽  
Yasunao Hattori ◽  
Atsushi Kawamura ◽  
Hidefumi Makabe
Keyword(s):  
Double Bond ◽  
Fire Ants ◽  
Chain Elongation ◽  
Piperidine Ring ◽  
Palladium Catalyzed

ABSTRACT Synthesis of (+)-solenopsin, a 2,6-disubstituted piperidine alkaloid, isolated from fire ants (Solenopsis), was achieved. Stereoselective construction of trans-2,6-piperidine ring moiety was performed using palladium-catalyzed cyclization. Chain elongation using Grubbs 2nd catalyst followed by the reduction of double bond and the deprotection of the Cbz group afforded (+)-solenopsin.

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