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Synfacts 2019; 15(07): 0753
DOI: 10.1055/s-0039-1689962
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Copper-Catalyzed Diels–Alder Cycloaddition

Contributor(s):
Mark Lautens
,
José F. Rodríguez
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
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Further Information

Publication History

Publication Date:
17 June 2019 (online)

 
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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.


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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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