Addition of Di(trimethylsilyl) Phosphite to Schiff Bases of 2,5-Diformylfuran

Authors

  • Jaroslaw Lewkowski Dept of Organic Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, POLAND
  • Marek Dziegielewski Dept of Organic Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, POLAND
  • Aleksandra Szczesniak Dept of Organic Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, POLAND
  • Magdalena Ciechanska Dept of Organic Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, POLAND

DOI:

https://doi.org/10.13171/mjc.1.3.2011.18.10.02

Abstract

A series of 2,5-Furanyl-bis-(aminomethylphosphonic Acids) has been synthesized by the addition of di(trimethylsilyl) phosphite to azomethine bond of achiral Schiff bases derved from 2,5-diformylfuran. The stereochemical aspect of this reaction has been studied and compared with the behaviour of achiral terephthalic Schiff bases in similar reaction. Whereas, addition to achiral terephthalic Schiff bases was found to be highly stereoselective, the analogous reaction with achiral 2,5-diformylfuran Schiff bases was stereoselective exclusively in the case when the substituent is benzyl.

References

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Published

2011-10-18

Issue

Vol. 1 No. 3 (2011)

Section

Organic Chemistry

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