Reaction Details

Organocatalytic Diels-Alder Reaction; Enantioselective Imidazolidinone Organocatalysis

Highly enantioselective Diels-Alder reaction between an α,β-unsaturated carbonyl dienophile and a conjugated diene catalyzed by MacMillan's Imidazolidinone Catalysts:

Organocatalytic Diels-Alder Reaction; Enantioselective Imidazolidinone Organocatalysis

Diels-Alder reactions with ketones: A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc.124, 2458 (2002)10.1021/ja017641u11890793. Intramolecular Diels-Alder reaction: R. M. Wilson et al., ibid.127, 11616 (2005)10.1021/ja054008q16104734. Natural product syntheses utilizing cascade cyclizations with propynal : S. B. Jones et al., ibid.131, 13606 (2009)10.1021/ja906472m19725517; eidem, Nature475, 183 (2011)10.1038/nature1023221753848.

The broadly general strategy of Enantioselective Imidazolidinone Organocatalysis utilizes MacMillan's catalysts for aldehyde transformations. Both lowest unoccupied molecular orbital (LUMO)-lowering iminium activation and singly occupied molecular orbital (SOMO) catalysis enable a wide array of asymmetric reactions:

Organocatalytic Diels-Alder Reaction; Enantioselective Imidazolidinone Organocatalysis

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