Application

No.120
Useful Dienophile
A1579 3-Acryloyl-2-oxazolidinone (1) 1g

3-Acryloyl-2-oxazolidinone (1) is a dienophile that is useful in the asymmetric Diels-Alder reaction. The dienophile 1 reacts with various dienes in the presence of chiral Lewis acids to form chiral Diels-Alder cycloadducts. The prepared adducts are used for the syntheses of various biologically active substances. For example, Evans and his coworkers used 1 in the asymmetric syntheses of ent-shikimic acids, and ent-Δ1-tetra-hydrocannabinol.1)

References

1) Enantioselective Diels-Alder reaction
a) D. A. Evans, D. M. Barnes, Tetrahedron Lett., 38, 57 (1997).
b) D. A. Evans, E. A. Shaughnessy, D. M. Barnes, Tetrahedron Lett., 38, 3193 (1997).
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