Structural assignment of a bis-cyclopentenyl--cyanohydrin formed via alkene metathesis from either a triene or a tetraene precursor

被引：4

作者：

Andrews, Keith G. ^{[1
]}

Frampton, Christopher S. ^{[2
]}

Spivey, Alan C. ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, London SW7 2AZ, England

[2] Pharmorphix Ltd, Cambridge CB4 0WE, England

来源：

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY | 2013年 / 69卷

关键词：

crystal structure; euonyminol; alkene metathesis; ring-closing metathesis (RCM); ring-opening metathesis (ROM); density functional theory (DFT); NMR prediction; RING-CLOSING METATHESIS; DIALLYLIC ALCOHOLS; STEREOCHEMISTRY; DECALINS;

D O I：

10.1107/S010827011302492X

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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--cyanohydrin [1-(1-hydroxycyclopent-3-en-1-yl)cyclopent-3-ene-1-carbonitrile, C11H13NO] rather than the trans-2,3,6,7-dehydrodecalin--cyanohydrin.

引用

页码：1207 / +

页数：12

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