Construction of spirocycles containing highly substituted pyrroli-dine and 1-indanone motifs with spiro quaternary stereogenic centers via 1,3-dipolar cycloaddition of 2-alkylidene-1-indanone and azomethine ylides promoted by simple imidazolium salts

RSC Advances ◽  
2015 ◽  
Vol 5 (87) ◽  
pp. 70910-70914 ◽  
Author(s):  
Wei-Qiang Hu ◽  
Yan-Su Cui ◽  
Zhi-Jun Wu ◽  
Chuan-Bao Zhang ◽  
Pei-Hao Dou ◽  
...  
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Imidazolium Salts ◽  
Stereogenic Centers ◽  
Quaternary Stereogenic Centers

The 1,3-dipolar cycloaddition of 2-alkylidene-1-indanone with azomethine ylides has been successfully developed promoted by simple imidazolium salts to construct a variety of spirocycles, containing highly substituted pyrrolidines, in excellent yields (up to 99%).

Organocatalytic synthesis of chiral CF3-containing oxazolidines and 1,2-amino alcohols: asymmetric oxa-1,3-dipolar cycloaddition of trifluoroethylamine-derived azomethine ylides

2020 ◽  
Vol 7 (21) ◽  
pp. 3452-3458
Author(s):  
Wen-Run Zhu ◽  
Qiong Su ◽  
Ning Lin ◽  
Qing Chen ◽  
Zhen-Wei Zhang ◽  
...  
Keyword(s):  
Amino Alcohols ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Stereogenic Centers

A series of CF3-containing oxazolidines were constructed via organocatalytic asymmetric oxa-1,3-dipolar cycloaddition. These oxazolidines could undergo facile conversion to CF3-containing 1,2-amino alcohols with vicinal stereogenic centers.

Copper/GanPhos-Catalyzed 1,3-Dipolar Cycloaddition of Azo­methine Ylides: An Efficient Access to Chiral Pyrrolidine Spirocycles

Synthesis ◽  
2020 ◽  
Author(s):  
Zhenjie Gan ◽  
Er-Qing Li ◽  
Ke Li ◽  
Hui Zhang
Keyword(s):  
Optically Active ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Reaction Conditions ◽  
Highly Efficient ◽  
Efficient Access ◽  
Stereogenic Centers

AbstractA highly efficient copper/GanPhos-catalyzed 1,3-dipolar cyclo­addition­ of azomethine ylides is reported. This viable transformation provides a series of optically active spiro[dihydronaphthalene-2,3′-pyrrolidine]s, bearing one spiro quaternary and three tertiary stereogenic centers, in good yields and with high ee values. This protocol features high diastereo- and enantioselectivity, broad substrate scope and mild reaction conditions.

scholarly journals An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy

2016 ◽  
Vol 12 ◽  
pp. 2240-2249 ◽  
Author(s):  
Alexei N Izmest’ev ◽  
Galina A Gazieva ◽  
Natalya V Sigay ◽  
Sergei A Serkov ◽  
Valentina A Karnoukhova ◽  
...  
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Stereogenic Centers ◽  
Isatin Derivatives

An effective and highly regio- and diastereoselective one-pot method for the synthesis of new polynuclear dispiroheterocyclic systems with five stereogenic centers (dispiro[imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-6,3′-pyrrolidine-2′,3′′-indoles]) comprising pyrrolidinyloxindole and imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine moieties has been developed. The method relies on a 1,3-dipolar cycloaddition of azomethine ylides generated in situ from isatin derivatives and sarcosine to 6-benzylideneimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7-diones.

Cu(i)/TF–BiphamPhos-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with dimethyl itaconate and 2-methyleneglutarate

RSC Advances ◽  
2014 ◽  
Vol 4 (32) ◽  
pp. 16899-16905 ◽  
Author(s):  
Hai-Yan Tao ◽  
Zhao-Lin He ◽  
Yang Yang ◽  
Chun-Jiang Wang
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Stereogenic Centers ◽  
Efficient Construction ◽  
Catalytic Asymmetric ◽  
Dimethyl Itaconate

Catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides with dimethyl itaconate and 2-methyleneglutarate was realized with Cu(i)/TF–BiphamPhos complex as the catalyst for the efficient construction of pyrrolidine derivatives bearing one unique all carbon-quaternary and two tertiary stereogenic centers.

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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