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Synfacts 2011(9): 0972-0972  
DOI: 10.1055/s-0030-1260863
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

New Ligand for Inverse-Electron-Demand Hetero-Diels-Alder Reaction

Contributor(s): Hisashi Yamamoto, Jiajing Tan
A. Barba, S. Barroso, G. Blay*, L. Cardona, M. Melegari, J. R. Pedro*
Universitat de València, Spain
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Publication History

Publication Date:
19 August 2011 (online)

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Significance

A new hydroxyl oxazoline derived from ketopinic acid was developed and successfully used for catalyzing the asymmetric hetero-­Diels-Alder cycloaddition of enol ethers and β,γ-unsaturated α-keto esters. Unprecedented exo selectivity was obtained with 2,4-trans-disubstituted chiral 2,3-dihydropyrans with up to 88% ee.