The first general enantioselective catalytic Diels-Alder reaction with simple (α,β-unsaturated ketones

Alan B. Northrup, David W.C. MacMillan

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459 Scopus citations


The first general approach to enantioselective catalysis of the Diels-Alder reaction with simple ketone dienophiles has been accomplished. The use of iminium catalysis has enabled enantioselective access to a fundamental Diels-Alder reaction variant that has previously been unavailable using chiral Lewis acid catalysis. A new chiral amine catalyst has been developed that allows a variety of monodentate cyclic and acyclic ketones to successfully participate in enantioselective [4 + 2] cycloadditions. A wide spectrum of cyclic and acyclic diene substrates can also be accommodated in this new organocatalytic transformation. A computational model is provided that is in accord with the sense of enantioinduction observed for all reactions conducted during the course of this study.

Original languageEnglish (US)
Pages (from-to)2458-2460
Number of pages3
JournalJournal of the American Chemical Society
Issue number11
StatePublished - Mar 20 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry


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