Tandem Cyclization Reaction between Optically Activeγ-Nitro Ketone and Chalcone towards the Synthesis of Chiral Cyclohexane Skeletons Bearing Five Stereocenters
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Stereocenter
Chalcone
Tandem
Cascade reaction
Methyl Ketone
Stereocenter
Asymmetric induction
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This work has demonstrated that a previously unexplored approach to separation of enantiomers via formation of diastereomeric derivatives with three stereogenic centers has obvious practical potential and deserves further systematic study. The design reported here is based on the unusual application of a configurationally unstable stereogenic nitrogen, which plays a key role in setting up the stereochemical match between the three stereogenic centers in the corresponding products.
Stereocenter
Diastereomer
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An efficient and powerful organocatalytic cascade reaction was achieved for the synthesis of biologically important chiral spiro[pyrrolidin-3,2′-oxindoles] using very simple and readily available starting materials. Three C–C bonds and four contiguous stereogenic centers including one quaternary stereocenter were established in a single operation with reasonable yields and good stereoselectivity.
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Oxindole
Cascade reaction
Reaction conditions
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A new Ag2O-promoted cascade reaction of 4-hydroxycoumarins with α-keto acids under mircowave irradiation has been developed. The reaction provides an efficient approach to fused chromenes with quaternary stereocenters in 10 min, and gives good yields. Chromene derivatives can be prepared on a gram scale using this method.
Stereocenter
Cascade reaction
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Stereocenter
Molar ratio
Chlorine atom
Proton NMR
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A highly enantioselective cascade reaction of benzotriazoles with nitroolefin-containing enonates catalyzed by a base/acid bifunctional organocatalyst has been developed. This cascade sequence affords efficient access to densely functionalized chiral chromans with a quaternary stereogenic center in high yield (up to 91%) with excellent enantioselectivity (up to 96% ee) and diastereoselectivity (up to 96:4 dr). The reaction itself features simple experimental procedures under benign conditions and is completely atom-economic in character.
Stereocenter
Cascade reaction
Quaternary carbon
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A triple Michael/aldol cascade reaction has been established to construct tetracyclic chromanes possessing six consecutive stereocenters.
Stereocenter
Domino
Aldol reaction
Cascade reaction
Michael reaction
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This chapter describes briefly optically active sulfur-containing derivatives whose chirality results from the presence of a stereogenic sulfur atom with different valency and coordination numbers. Thus, it updates the more or less rich literature reports on the most common approaches that have made it possible to isolate them as optically active forms. Their recent synthetic applications are also illustrated.
Stereocenter
Valency
Chirality
Center (category theory)
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Stereocenter
Diastereomer
Atropisomer
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