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Design of Chiral N-Triflyl Phosphoramide as a Strong Chiral Brønsted Acid and Its Application to Asymmetric Diels-Alder Reaction

Daisuke Nakashima and Hisashi Yamamoto*

*Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, Email:

D. Nakashima, H. Yamamoto, J. Am. Chem. Soc., 2006, 128, 9626-9627.

DOI: 10.1021/ja062508t


A highly reactive and acidic chiral N-triflyl phosphoramide was used as a Brønsted acid for a highly enantioselective Diels-Alder reaction of an α,β-unsaturated ketone with various silyloxydienes.

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Key Words

Diels-Alder Reaction

ID: J48-Y2006-2400