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Journal of the Chemical Society, Perkin Transactions 1, 2001
Following the generation of azomethine ylide 3 from the β-lactam-based oxazolidinone 1, a series of alternative entries to this and related 1,3-dipoles have been explored. The first approach is based on the use of monocyclic azetidinones 6–12 and 14 carrying a leaving group at C(4) and an activated (acidic) proton adjacent to the ring nitrogen ...
Brown, D +6 more
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Following the generation of azomethine ylide 3 from the β-lactam-based oxazolidinone 1, a series of alternative entries to this and related 1,3-dipoles have been explored. The first approach is based on the use of monocyclic azetidinones 6–12 and 14 carrying a leaving group at C(4) and an activated (acidic) proton adjacent to the ring nitrogen ...
Brown, D +6 more
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Oxazoline route to azomethine ylides
Journal of the American Chemical Society, 1986Etude de la generation de N-alhylidene ammonioethylenolates a partir d'oxazolines-4; les betaines sont piegees par cycloadditions avec le butynedioate de dimethyle ou l'acrylate de ...
Edwin. Vedejs, Janet Wisniewski. Grissom
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Synthesis and Use of a Trifluoromethylated Azomethine Ylide Precursor
The Journal of Organic Chemistry, 2012The presence of fluorous substituents can impart a dramatic effect on the efficacy of molecules used for a range of applications in society. Here, we describe the preparation and use of a new trifluoromethylated azomethine ylide precursor, which leads to a series of fluorinated pyrrolidine, 3-pyrroline, and pyrrole building blocks.
Gaël, Tran +4 more
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Enantioselective Cycloadditions of Azomethine Ylides
2008The asymmetric 1,3-DCR of azomethine ylides, which is generated from the corresponding imino ester and alkenes, is one of the most fascinating transformations because the configuration of the four new stereogenic centers of the finally obtained proline can be absolutely established in only one step with total atom economy.
Carmen Nájera, José M. Sansano
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Reaction of Functionalized Azomethine Ylides with Olefinic Dipolarophiles
HETEROCYCLES, 2006AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
Keisuke Kawashima +2 more
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Recent Advances in Azomethine Ylide Chemistry
1989Publisher Summary Azomethine ylides are planar molecules composed of one nitrogen and two terminal sp2 carbons. At most, four geometrical isomers are possible for these transient molecules. Their cycloadditions to olefin or acetylene dipolarophiles give rise to the formation of two sets of carbon-carbon bonds in a single step.
Otohiko Tsuge, Shuji Kanemasa
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Fused aziridines as sources of azomethine ylides
Chemistry of Heterocyclic Compounds, 2012The use of fused aziridines as sources of azomethine ylides in the synthesis of polyheterocyclic compounds is examined. Features of thermo- and photolytic opening of aziridines and aspects of the stereo-, regio-, and chemoselectivity of cycloaddition and electrocyclization of azomethine ylides are discussed.
A. F. Khlebnikov, M. S. Novikov
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A dehydrogenation route to azomethine ylides and isoindoles
Journal of the Chemical Society, Perkin Transactions 1, 1989Dehydrogenation of methyl 1,2,3,4-tetrahydroisoquinolin-2-yl- and β-carbolin-9-yl-acetates with palladium black in dimethylformamide generates anti-azomethine ylides stereospecifically. The analogous reaction with methyl isoindolin-2-ylacetate gives the corresponding isoindole. Both types of product can be trapped by N-methylmaleimide. The mechanism of
Ronald Grigg, Frances Heaney
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