Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5264928 | Tetrahedron Letters | 2012 | 4 Pages |
Abstract
A convenient approach to the construction of dihydroxylated unsaturated azepanes featuring a functional group (ethoxycarbonyl)methyl or (cyano)methyl at C-2 was achieved from a pent-4-enal synthon obtained in four steps from d-xylose. The key step of the sequence relied on the conjugate addition of allylamine to α,β-unsaturated ester or nitrile, prepared by Wadsworth-Emmons olefination. Subsequent RCM afforded the target unsaturated azepanes.
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Authors
Sophie Goumain, Hanaa Taghzouti, Charles Portella, Jean-Bernard Behr, Richard Plantier-Royon,