Unknown

Dataset Information

0

Enantioselective Synthesis of Hydrobenzofuranones Using an Asymmetric Desymmetrizing Intramolecular Stetter Reaction of Cyclohexadienones.

ABSTRACT: A series of cyclohexadienones were synthesized by dearomatization of phenols followed by Dess-Martin oxidation. Asymmetric intramolecular Stetter reactions of these substrates provide hydrobenzofuranones in good to excellent yields and excellent stereoselectivities. Up to three stereocenters as well as quaternary stereocenter are formed from polysubstituted substrates. A scale up experiment demonstrates the utility of this transformation.

SUBMITTER: Liu Q 

PROVIDER: S-EPMC2709411 | biostudies-literature | 2007

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Enantioselective Synthesis of Hydrobenzofuranones Using an Asymmetric Desymmetrizing Intramolecular Stetter Reaction of Cyclohexadienones.

Liu Qin Q   Rovis Tomislav T  

Organic process research & development 20070101 3

A series of cyclohexadienones were synthesized by dearomatization of phenols followed by Dess-Martin oxidation. Asymmetric intramolecular Stetter reactions of these substrates provide hydrobenzofuranones in good to excellent yields and excellent stereoselectivities. Up to three stereocenters as well as quaternary stereocenter are formed from polysubstituted substrates. A scale up experiment demonstrates the utility of this transformation. ...[more]

Similar Datasets

Unknown Asymmetric synthesis of hydrobenzofuranones via desymmetrization of cyclohexadienones using the intramolecular Stetter reaction.
| S-EPMC2701296 | biostudies-literature
Unknown Enantioselective desymmetrization of cyclohexadienones via an intramolecular Rauhut-Currier reaction of allenoates.
| S-EPMC5059449 | biostudies-literature
Unknown Scope of the asymmetric intramolecular stetter reaction catalyzed by chiral nucleophilic triazolinylidene carbenes.
| S-EPMC4222522 | biostudies-literature
Unknown Mechanistic investigation of the enantioselective intramolecular stetter reaction: proton transfer is the first irreversible step.
| S-EPMC3064720 | biostudies-other
Unknown Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates.
| S-EPMC2684863 | biostudies-literature
Unknown Catalytic asymmetric stetter reaction onto vinylphosphine oxides and vinylphosphonates.
| S-EPMC2746454 | biostudies-literature
Unknown A photoisomerization-coupled asymmetric Stetter reaction: application to the total synthesis of three diastereomers of (-)-cephalimysin A.
| S-EPMC3820004 | biostudies-literature
Unknown Enantioselective synthesis of (-)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction.
| S-EPMC4756631 | biostudies-literature
Unknown Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes.
| S-EPMC2996425 | biostudies-other
Unknown Enantioselective Total Synthesis of (-)-Finerenone Using Asymmetric Transfer Hydrogenation.
| S-EPMC7839499 | biostudies-literature