Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 8, Pages 980-989Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201701578
Keywords
Fragrances; Vetiver; Spiro compounds; Cycloisomerisation; Heterogeneous catalysis
Categories
Funding
- French ANR ALEA project [ANR-2013-ALEA-009-01]
- Universite Nice-Sophia Antipolis
- Centre National de la Recherche Scientifique (CNRS)
Ask authors/readers for more resources
The Lewis superacid-catalysed cascade cyclisation of enol ethers derived from campholenal resulted in an elegant reaction leading to new elaborated spirocyclic ethers. Under identical conditions, the reaction proceeded by two distinct mechanisms, depending on the relative configuration of the starting substrate. Hence, either a tandem cyclisation process gave access to tetracyclic spirodiethers, while another process involving a less common reaction sequence (cyclisation/1,4-hydride shift) led to complex tricyclic spiroalcohols and/or spiroketones. Investigations on synthetic intermediates by enantioselective gas chromatography permitted to assess the high stereospecificity of the process. Collectively, these expedite syntheses gave access to unprecedented spiroxides which displayed, in some instances, strong vetiver-like olfactory notes. While campholenic derivatives have long been used in the industrial production of fragrant sandalwood substitutes, these new derivatives provide potential synthetic alternatives to the esteemed natural ingredient vetiver.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available