Organocatalytic Asymmetric Wittig Reactions: Generation of Enantioenriched Axially Chiral Olefins Breaking a Symmetry Plane

Abstract The first catalytic asymmetric Wittig reaction is presented. Hydrogen-bond donors catalyze the [2+2] cycloaddition reaction between stabilized phosphorus ylides and 4-substituted cyclohexanones, breaking their symmetry plane and furnishing axially chiral olefins with moderate stereoselectiv...

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Bibliographic Details
Published in:Synlett 2011-11, Vol.2011 (18), p.2745-2749
Main Authors: Gramigna, Lucia, Duce, Sara, Filippini, Giacomo, Fochi, Mariafrancesca, Franchini, Mauro Comes, Bernardi, Luca
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
letter
Organic chemistry
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:Abstract The first catalytic asymmetric Wittig reaction is presented. Hydrogen-bond donors catalyze the [2+2] cycloaddition reaction between stabilized phosphorus ylides and 4-substituted cyclohexanones, breaking their symmetry plane and furnishing axially chiral olefins with moderate stereoselectivities.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0031-1289516