Work

Single-crystal X-ray diffraction analysis and mechanistic implications of (2 R ,3 R )-2-(2-phenoxyethyl)tetrahydrofuran-3-yl acetate

Year: 2025

Type: article

Abstract: Our laboratory recently explored a highly stereospecific rearrangement of epoxides into tetrahydrofurans. To unambiguously determine the stereochemical outcome of this rearrangement, single crystals of one of the products, (2 R *,3 R *)-2-(2-phenoxyethyl)tetrahydrofuran-3-yl acetate, C 14 H 18 O 4 , were grown and analyzed. Based on the crystal structure data, we were able to show that the contiguous stereocenters of this molecule are in a syn configuration, and we now suggest with confidence a plausible mechanism for the rearrangement reaction. The syn configuration of the ring may also account for the inability of most members of this class to crystallize, as it imparts a kink in the structure reminiscent of low-melting unsaturated fatty acids.

Source: Acta Crystallographica Section C Structural Chemistry

DOI: 10.1107/s2053229625010150

Authors: Steven P. Kelley, Appasaheb K. Nirpal, Shyam Sathyamoorthi

Institutions: University of Missouri, University of Kansas

Language: English

Topic: Crystal structures of chemical compounds

Subfield: Inorganic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Awards: G4233733361, G5036224426, G9000165440, G9000295040, Tethered aza-Wacker Technology for Complex Antibiotic Assembly