Organocatalytic Enantioselective [3+2] Cycloaddition of Azomethine Ylides with 2,4‐Dienals: Construction of Remote Stereogenic Centers via 1,6‐Addition Reaction

2020 ◽  
Vol 362 (24) ◽  
pp. 5716-5720
Author(s):  
Hui Jiang ◽  
Leijie Zhou ◽  
Biming Mao ◽  
Chunhao Yuan ◽  
Wei Wang ◽  
...  
Keyword(s):  
Addition Reaction ◽  
Azomethine Ylides ◽  
Stereogenic Centers

Ultrasound-Promoted Synthesis of Spirocyclopropanes from Switchable Starting Materials via Azomethine Ylide [3+2]-Cycloaddition

Synthesis ◽  
2021 ◽  
Author(s):  
Issa Yavari ◽  
Sara Sheikhi ◽  
Jamil Sheykhahmadi ◽  
Zohreh Taheri ◽  
Mohammad Reza Halvagar
Keyword(s):  
Single Crystal ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
X Ray ◽  
Green Protocol ◽  
Stereogenic Centers ◽  
Quinoxaline Derivatives ◽  
Excellent Selectivity

AbstractAn ultrasound-promoted green protocol to access a new series of spirocyclopropanes from indeno[1,2-b]quinoxaline derivatives and azomethine ylides, generated in situ from the iodine-catalyzed reaction of acetophenones as well as of 2-methylquinoline with pyridine in the presence of a base, is described. These transformations proceed via a spirocyclopropanation reaction followed by elimination of pyridine. Clear evidence for the structure of a spirocyclopropane-linked indenoquinoxaline derivative was obtained from single-crystal X-ray analysis. The most important feature of this reaction is the fact it forms three stereogenic centers, one of which is quaternary, with excellent selectivity.

Tandem [3 + 2] Cycloaddition/1,4-Addition Reaction of Azomethine Ylides and Aza-o-quinone Methides for Asymmetric Synthesis of Imidazolidines

2017 ◽  
Vol 19 (19) ◽  
pp. 5236-5239 ◽  
Author(s):  
Hao Jia ◽  
Honglei Liu ◽  
Zhenyan Guo ◽  
Jiaxing Huang ◽  
Hongchao Guo
Keyword(s):  
Asymmetric Synthesis ◽  
Addition Reaction ◽  
Azomethine Ylides ◽  
Quinone Methides

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.

scholarly journals Organocatalytic one-pot 1,4-/1,6-/1,2-addition sequence for the stereocontrolled formation of six consecutive stereocenters

2015 ◽  
Vol 51 (12) ◽  
pp. 2270-2272 ◽  
Author(s):  
Pankaj Chauhan ◽  
Suruchi Mahajan ◽  
Gerhard Raabe ◽  
Dieter Enders
Keyword(s):  
Addition Reaction ◽  
One Pot ◽  
Stereogenic Centers

A new stereoselective organocatalyzed one-pot 1,4-/1,6-/1,2-addition reaction sequentially catalyzed by low loading of a squaramide and an achiral base provide a direct entry to isoxazole bearing cyclohexanes with six contiguous stereogenic centers in good yields and excellent stereoselectivities.

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.

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