Evans DA.
*
Miller SJ,
Lectka T.
Harvard University, Cambridge, USA
Bis(oxazoline)copper(II) Complexes as Chiral Catalysts for the Enantioselective Diels–Alder
Reaction.
J. Am. Chem. Soc. 1993;
115: 6460-6461
Key words
copper catalysis - Diels–Alder cycloaddition - Lewis acids
Significance
Following Narasaka’s report on titanium-catalyzed enantioselective Diels–Alder reactions
(J. Am. Chem. Soc. 1989, 111, 5340) and Corey’s variants using chiral magnesium(II) and iron(II) catalysts (J. Am. Chem. Soc. 1991, 113, 728; Tetrahedron Lett. 1992, 33, 6807), Evans disclosed a highly enantioselective Diels–Alder reaction employing
copper(II)-catalysts and BOX ligands.
Comment
Products were obtained in high yields and excellent enantioselectivities. This class
of chiral Lewis acid catalysts has since been applied to asymmetric aldol reactions,
Michael additions, and carbonyl ene reactions by the same group (J. S. Johnson, D.
A. Evans Acc. Chem. Res. 2000, 33, 325).
