Syntheses and Crystal Structures of Three Chiral Oxazolidinones with Different Ring Conformations

Ester Soru, Grace Cairney, John M. D. Storey, William T. A. Harrison* (Corresponding Author)

*Corresponding author for this work

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Abstract

The preparation of new, enantiomerically pure, α-amino acids from easily available starting materials is an ongoing challenge in synthetic organic chemistry. Here, we describe the syntheses and crystal structures of three chiral oxazolidinone derivatives prepared from L-alanine and pivalaldehyde to form a Schiff base intermediate and then reaction with the appropriate acid chloride to form the heterocycle. In each compound, the methyl and tert-butyl substituents lie to the same side of the molecule: these homochiral ‘cis’ structures were separated from their trans diastereomers by fractional crystallisation. The five-membered rings in these structures adopt various conformations including envelopes with either a C or O atom as the flap and twisted about a C–O bond. The extended structures of two of these compounds feature C(6) chains of molecules linked by C–H···O hydrogen bonds: one of these has a notably short H···O separation of 2.24 (3) Å.
Original languageEnglish
Article number1598
Number of pages10
JournalCrystals
Volume12
Issue number11
Early online date10 Nov 2022
DOIs
Publication statusPublished - 10 Nov 2022

Bibliographical note

Funding: This research received no external funding.
Acknowledgments: We thank the EPSRC National Crystallography Centre (University of Southampton) for the X-ray data collections.

Keywords

  • oxazolidinone
  • absolute structure
  • ring conformation
  • C–H···O hydrogen bonds

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