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Synfacts 2008(6): 0615-0615  
DOI: 10.1055/s-2008-1078402
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Applications of the Asymmetric Diels-Alder Reaction

Contributor(s): Mark Lautens, Frédéric Ménard
E. J. Hicken, E. J. Corey*
Harvard University, Cambridge, USA
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Publikationsdatum:
21. Mai 2008 (online)

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Significance

The authors report on the application of their previously developed catalytic Diels-Alder reaction in a natural product context (J. Am. Chem. Soc. 2007, 129, 1498). The reaction scope was extended to electron-rich dienes and proceeds stereoselectively to yield complex carbocyclic products under very mild conditions. Using the AlBr3 version of the chiral Lewis acid 3 was critical for the success of the reaction.