Pseudopeptidic sulfoxides: Relative stability and absolute configuration of diastereomers

Jean Marc Poudrel, Peter Karuso

Research output: Contribution to journalArticleResearchpeer-review

Abstract

The relative stability in solution of diastereomeric pseudopeptidic sulfoxides initially designed as FKBP inhibitors is used to assign the absolute configuration at the sulfur atom. Decomposition is shown to occur via β-elimination of the corresponding sulfenic acid and alkene. Complementary studies including molecular mechanics, 1H NMR spectroscopy and optical rotation confirm that the (R)-isomer is the most stable, presumably due to non-bonded interactions favouring a low energy conformation where decomposition is precluded.

LanguageEnglish
Pages6185-6189
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number32
Publication statusPublished - 5 Aug 2000

Fingerprint

Sulfenic Acids
Tacrolimus Binding Proteins
Sulfoxides
Optical Rotation
Alkenes
Mechanics
Sulfur
Magnetic Resonance Spectroscopy
Optical rotation
Decomposition
Molecular mechanics
Isomers
Nuclear magnetic resonance spectroscopy
Conformations
Atoms
Proton Magnetic Resonance Spectroscopy

Keywords

  • Absolute configuration
  • Decomposition
  • Pyrolysis
  • Stability
  • Sulfoxide

Cite this

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Pseudopeptidic sulfoxides : Relative stability and absolute configuration of diastereomers. / Poudrel, Jean Marc; Karuso, Peter.

In: Tetrahedron Letters, Vol. 41, No. 32, 05.08.2000, p. 6185-6189.

Research output: Contribution to journalArticleResearchpeer-review

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