Intramolecular Diels−Alder and Tandem Intramolecular Diels−Alder/1,3-Dipolar Cycloaddition Reactions of 1,3,4-Oxadiazoles
Journal of the American Chemical Society2002Vol. 124(38), pp. 11292–11294
Citations Over TimeTop 10% of 2002 papers
Gordon Wilkie, Gregory I. Elliott, Brian S. J. Blagg, S. E. Wolkenberg, D. R. Soenen, Michael M. Miller, Scott R. Pollack, Dale L. Boger
Abstract
The scope of intramolecular Diels-Alder and a novel tandem Diels-Alder/1,3-dipolar cycloaddition cascade of 1,3,4-oxadiazoles is disclosed. In the cases examined, the tandem cycloadditions construct three new rings with formation of four new C-C bonds and set all six stereocenters about a central six-membered ring in a single step including three contiguous and four total quaternary centers without a trace of a second diastereomer.
Related Papers
- → Organocatalytic asymmetric multicomponent cascade reaction via 1,3-proton shift and [3+2] cycloaddition: an efficient strategy for the synthesis of oxindole derivatives(2013)138 cited
- → Enantioselective Synthesis of Chromans with a Quaternary Stereogenic Centre through Catalytic Asymmetric Cascade Reactions(2011)17 cited
- → Diastereoselective construction of tetracyclic chromanes via a triply annulative strategy(2022)6 cited
- → Asymmetric reduction of β‐ketoesters and chiral β‐iminoesters: Impact of a α‐quaternary stereocenter(2010)2 cited
- → ChemInform Abstract: Organocatalytic Cascade Michael/Michael Reaction for the Asymmetric Synthesis of Spirooxindoles Containing Five Contiguous Stereocenters.(2016)