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 journalArticlepeer-review

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

Fingerprint Dive into the research topics of 'Pseudoephedrine as a Chiral Auxiliary for Asymmetric Michael Reactions: Synthesis of 3-Aryl-δ-lactones'. Together they form a unique fingerprint.

Cite this