Structural assignment of a bis-cyclopentenyl-β-cyanohydrin formedviaalkene metathesis from either a triene or a tetraene precursor

Andrews, Keith G.; Frampton, Christopher S.; Spivey, Alan C.

Abstract

The identity of the major product of Ru-catalysed alkene metathesis of two polyene substrates has been determined using density functional theory (DFT) NMR prediction, a 1H–1H Total Correlated Spectroscopy (TOCSY) NMR experiment and ultimately by single-crystal X-ray crystallography. The substrates were designed as those that would potentially allow expedient access to the trans-deca­lin skeleton of the natural product (−)-euonyminol, but the product was found to be a bis-cyclo­pentenyl-β-cyano­hydrin [1-(1-hy­droxy­cyclo­pent-3-en-1-yl)cyclo­pent-3-ene-1-carbo­nitrile, C11H13NO] rather than the trans-2,3,6,7-de­hydro­deca­lin-β-cyano­hydrin.

Citation

Andrews, K. G., Frampton, C. S., & Spivey, A. C. (2013). Structural assignment of a bis-cyclopentenyl-β-cyanohydrin formedviaalkene metathesis from either a triene or a tetraene precursor. Acta crystallographica. Section C, Crystal structure communications, 69(11), 1207-1211. https://doi.org/10.1107/s010827011302492x

• Journal Article Type: Article
• Online Publication Date: Oct 9, 2013
• Publication Date: Nov 15, 2013
• Deposit Date: Apr 11, 2024
• Journal: Acta Crystallographica Section C Crystal Structure Communications
• Print ISSN: 0108-2701
• Electronic ISSN: 1600-5759
• Publisher: International Union of Crystallography
• Peer Reviewed: Peer Reviewed
• Volume: 69
• Issue: 11
• Pages: 1207-1211
• DOI: https://doi.org/10.1107/s010827011302492x
• Keywords: General Biochemistry, Genetics and Molecular Biology; General Medicine
• Public URL: https://durham-repository.worktribe.com/output/2382136