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

Soru, Ester; Cairney, Grace; Storey, John M. D.; Harrison, William T. A.

doi:10.3390/cryst12111598

Open AccessArticle

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

by

Ester Soru

,

Grace Cairney

,

John M. D. Storey

and

William T. A. Harrison

^*

Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, UK

^*

Author to whom correspondence should be addressed.

Crystals 2022, 12(11), 1598; https://doi.org/10.3390/cryst12111598

Submission received: 9 October 2022 / Revised: 26 October 2022 / Accepted: 8 November 2022 / Published: 10 November 2022

(This article belongs to the Section Organic Crystalline Materials)

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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.

Keywords: oxazolidinone; absolute structure; ring conformation; C–H···O hydrogen bonds

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MDPI and ACS Style

Soru, E.; Cairney, G.; Storey, J.M.D.; Harrison, W.T.A. Syntheses and Crystal Structures of Three Chiral Oxazolidinones with Different Ring Conformations. Crystals 2022, 12, 1598. https://doi.org/10.3390/cryst12111598

AMA Style

Soru E, Cairney G, Storey JMD, Harrison WTA. Syntheses and Crystal Structures of Three Chiral Oxazolidinones with Different Ring Conformations. Crystals. 2022; 12(11):1598. https://doi.org/10.3390/cryst12111598

Chicago/Turabian Style

Soru, Ester, Grace Cairney, John M. D. Storey, and William T. A. Harrison. 2022. "Syntheses and Crystal Structures of Three Chiral Oxazolidinones with Different Ring Conformations" Crystals 12, no. 11: 1598. https://doi.org/10.3390/cryst12111598

APA Style

Soru, E., Cairney, G., Storey, J. M. D., & Harrison, W. T. A. (2022). Syntheses and Crystal Structures of Three Chiral Oxazolidinones with Different Ring Conformations. Crystals, 12(11), 1598. https://doi.org/10.3390/cryst12111598

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

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