Pseudoephedrine as a Chiral Auxiliary for Asymmetric Michael Reactions: Synthesis of 3-Aryl-δ-lactones

Jacqueline H. Smitrovich, Geneviève N. Boice, Chuanxing Qu, Lisa DiMichele, Todd D. Nelson, Mark A. Huffman, Jerry Murry, James McNamara, Paul J. Reider

Research output: Contribution to journalArticle

30 Scopus citations

Abstract

(Equation Presented) The asymmetric Michael reaction of pseudoephedrine amides is reported. The 1,5-dicarbonyl products are converted to 3-aryl-δ-lactones in a two-step reduction/lactonization sequence. This method provides access to enantiomerically enriched trans-3,4-disubstituted δ-lactones.

Original languageEnglish (US)
Pages (from-to)1963-1966
Number of pages4
JournalOrganic Letters
Volume4
Issue number11
DOIs
StatePublished - May 30 2002
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Smitrovich, J. H., Boice, G. N., Qu, C., DiMichele, L., Nelson, T. D., Huffman, M. A., Murry, J., McNamara, J., & Reider, P. J. (2002). Pseudoephedrine as a Chiral Auxiliary for Asymmetric Michael Reactions: Synthesis of 3-Aryl-δ-lactones. Organic Letters, 4(11), 1963-1966. https://doi.org/10.1021/ol0259847