Assembly of fluorinated chromanones via enantioselective tandem reaction

Abstract

The enantioselective synthesis of fluorinated tricyclic chromanones with multiple vicinal stereogenic centers has been realized for the first time, through the tandem reaction between 2-fluorinated 1-(2-hydroxyaryl)-1,3-diketones and α,β-unsaturated aldehydes. In...

Strategies and Methods for the Catalytic Asymmetric Synthesis of Benzofuran/Benzopyran Fused Acetals: A Review

“…Subsequently, we further expanded the scope of this work by applying fluorine‐containing substrates 61 [51] . Moreover, replacing the final oxidation of the tandem process with acylation reaction could also avoid epimerization in this work.…”

“…Subsequently, we further expanded the scope of this work by applying fluorine-containing substrates 61. [51] Moreover, replacing the final oxidation of the tandem process with acylation reaction could also avoid epimerization in this work. The same configuration of products indicated that very similar transition state has been involved in all cases (Scheme 31).…”

The Asymmetric Synthesis of Polycyclic Tetrahydroxanthone via the Cascade Reaction of Alkene‐Substituted 1,3‐diketones and Alkenyloxindoles

“…In the past few years, we have been interested in the stereoselective construction of valuable heterocycles with multi-stereocenters via organocatalyzed domino reactions. [14] As part of our ongoing efforts, we conducted an organocatalyzed stereoselective domino reaction of isatylidene malononitriles and alkenesubstituted 1,3-diketones to provide a facile approach to construction of complex tetrahydroxanthone framework with three contiguous stereocenters. [14d] Considering the potential applications of this skeleton, developing new catalytic systems to realize the diversityoriented construction of chiral tetrahydroxanthone scaffold is still meaningful.…”

Asymmetric Synthesis of Multicyclic Spirooxindole Derivatives Bearing Stereogenic Quaternary Carbon Atoms

“…However, aryl- or alkenyl-substituted acyclic diketones have not been successfully reported for this [3 + 3] cycloaddition . As part of our continuous interest in the construction of O , O -acetal-fused tricyclic skeletons using 1-(2-hydroxyaryl)-1,3-butanediones through organocatalyzed domino reaction, we attempted to construct the spiropyran–oxindole skeleton bearing an O , O -acetal-fused tricyclic motif through the domino reaction between 1-(2-hydroxyaryl)-1,3-butanediones and isatylidene malononitriles (Scheme b).…”