A Modular Four-Component Route To Substituted 1,7,9-Decatrien-3-Ones Using A Chloro-Substituted Phosphorane As Key C-3 Building Block
SYNTHESIS-STUTTGART(2016)
Abstract
An efficient and flexible four-component route to substituted 1,7,9-decatrien-3-ones was established by alkylation of sodium dialkyl malonates with a chloro-substituted phosphorane followed by a Wittig reaction with the corresponding carbonyl compound. The resulting enones were alkylated at their malonate unit with sorbyl bromide to give the title compounds in good overall yields. In an attempt to improve the overall yield by using in situ generated sorbyl tosylate we discovered the formation of an unusual bicyclic product with a 3-oxocyclopenta[b]furan core that is formally generated by an oxidative dimerization of the employed precursor enone. The structure of this compound was unambiguously determined by an X-ray crystal analysis.
MoreTranslated text
Key words
alkylation, dialkyl malonate, olefination, phosphorane, ring closure
AI Read Science
Must-Reading Tree
Example
![](https://originalfileserver.aminer.cn/sys/aminer/pubs/mrt_preview.jpeg)
Generate MRT to find the research sequence of this paper
Chat Paper
Summary is being generated by the instructions you defined