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Reaction discovery using microfluidic-based multidimensional screening of polycyclic iminium ethers.

Jennifer L Treece1, John R Goodell, David Vander Velde

  • 1Department of Medicinal Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, 4070 Malott Hall, Lawrence, Kansas 66045, USA.

The Journal of Organic Chemistry
|February 19, 2010
PubMed
Summary

Researchers explored polycyclic iminium ethers, discovering new reaction pathways for generating functionalized lactams. Automated microfluidics enabled efficient screening to expand chemical diversity from these versatile intermediates.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Polycyclic iminium ethers are versatile electrophilic intermediates.
  • Their reactivity with nucleophiles is condition-dependent, yielding functionalized lactams.

Purpose of the Study:

  • To expand the reactivity scope of polycyclic iminium ethers.
  • To discover novel chemotypes through reaction screening.

Main Methods:

  • Automated microfluidics reaction platform utilized for high-throughput screening.
  • Systematic investigation of iminium ether reactions with various nucleophiles.

Main Results:

  • Identified several novel and interesting reaction pathways for iminium ether intermediates.
  • Demonstrated the utility of automated screening for discovering new synthetic routes.

Conclusions:

  • Automated microfluidics is an effective tool for exploring complex chemical reactivity.
  • New synthetic methodologies were uncovered for accessing diverse lactam structures.