Cu(OTf)2-promoted efficient synthetic route towards glycospiro-pyrrolo[2,1-a]isoquinolines

Barman, Piyali Deb; Sanyal, Ishita; Mandal, Sukhendu; Banerjee, Anindyajit

doi:10.1016/j.tetlet.2014.08.076

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Exocyclic Unsaturated 2π-electron Components1

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Cited by 4 publications

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“…Glycospiro-2,3-dihydropyrrolo[2,1- a ]isoquinolines 206 were synthesized by the reaction of 3-deoxy-3- C -[( Z )-(methoxycarbonyl)methylene]-1,2:5,6-di- O -isopropylidene- α - D -glucofuranose 205 with isoquinoline-based azomethine ylide formed from isoquinolines 11 and alkyl bromoacetates or 2-bromoacetophenones 204 in the presence of Cu(OTf) 2 –Et 3 N as a catalyst ( Scheme 70 ) [ 102 ].…”

Section: Exocyclic Unsaturated 2π-electron Componentsmentioning

confidence: 99%

Azomethine Ylides—Versatile Synthons for Pyrrolidinyl-Heterocyclic Compounds

et al. 2023

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Azomethine ylides are nitrogen-based three-atom components commonly used in [3+2]-cycloaddition reactions with various unsaturated 2π-electron components. These reactions are highly regio- and stereoselective and have attracted the attention of organic chemists with respect to the construction of diverse heterocycles potentially bearing four new contiguous stereogenic centers. This review article complies the most important [3+2]-cycloaddition reactions of azomethine ylides with various olefinic, unsaturated 2π-electron components (acyclic, alicyclic, heterocyclic, and exocyclic ones) reported over the past two decades.

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Section: Exocyclic Unsaturated 2π-electron Componentsmentioning

confidence: 99%