One Step Selective Counterion Dependent Formation of Conjugated Chiral N-Sulfinylimines from Aldehydes

Jeffrey R. Groch, Nicholas R. Lauta, Jon T. Njardarson

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

We report a detailed study on the synthesis and aldehyde vinylogation applications of chiral N-sulfinyl imine phosphonate reagents. Two complementary scalable reagent routes, from trialkyl phosphites and methyl phosphonates, respectively, are presented. This reagent class enables significant streamlining in synthesis of conjugated Ellman imines from aldehydes, which can now be accomplished in a single step compared to a more classic 4-step redox-based approach. Aldehyde vinylogation optimizations have revealed significant counterion effects and unexpected competing reaction challenges that needed to be addressed to achieve high yields.

Original languageEnglish (US)
Pages (from-to)395-399
Number of pages5
JournalOrganic Letters
Volume25
Issue number2
DOIs
StatePublished - Jan 20 2023
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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