Highly enantioselective formal aza-Diels-Alder reactions with acylhydrazones and Danishefsky's diene promoted by a silicon Lewis acid

Sharon K. Lee, Uttam K. Tambar, Nicholas R. Perl, James L. Leighton

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

Silicon Lewis acid 3 is effective for the promotion of highly enantioselective cycloaddition reactions of acylhydrazones with Danishefsky's diene (formal aza-Diels-Alder reactions). The reactions are conducted at ambient temperature for 15 min, and produce the products in good yield and with high levels of enantioselectivity. A remarkable solvent-dependent reversal in the sense of absolute stereochemical induction has been observed. The method has been applied to an efficient and stereoselective synthesis of the neurokinin 1 receptor antagonist casopitant.

Original languageEnglish (US)
Pages (from-to)4769-4774
Number of pages6
JournalTetrahedron
Volume66
Issue number26
DOIs
StatePublished - Jun 26 2010

Keywords

  • Acylhydrazones
  • Aza-Diels-Alder
  • Casopitant
  • Danishefsky's Diene
  • Silicon Lewis Acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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