A novel route to functionalized dendralenes with an allylsilane as integral component has been developed. The key step involves a dimethylsulfonium methylide mediated olefination of appropriately substituted silylmethylethenylidene phosphonoacetate followed by Horner–Wadsworth–Emmons reaction with aromatic aldehydes. The tri- and tetra substituted dendralenes are stable towards self Diels–Alder cyclodimerization which can be attributed to stereoelectronic effect of the silylmethyl group favoring for an unreactive conformation.
|Number of pages||7|
|Journal||Proceedings of the National Academy of Sciences India Section A - Physical Sciences|
|State||Published - 1 Dec 2016|
- Dimethylsulfonium methylide
- Stable dendralenes