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Synfacts 2019; 15(07): 0753
DOI: 10.1055/s-0039-1689962
DOI: 10.1055/s-0039-1689962
Metals in Synthesis
Enantioselective Copper-Catalyzed Diels–Alder Cycloaddition
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
17. Juni 2019 (online)
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.
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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).
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