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- Title
Lewis Acid‐Mediated Decarboxylative Allylation of Enol Carbonates.
- Authors
Dokai, Yoichi; Nishizawa, Takuma; Saito, Kodai; Yamada, Tohru
- Abstract
A homoallylic ketone can be transformed and functionalized by various synthetic reactions, and thus, is regarded as one of the representative building blocks in organic chemistry. An additional route to access homoallylic ketones, namely, a Lewis acid‐mediated decarboxylative allylation of cyclic enol carbonates, prepared by fixation of carbon dioxide onto propargyl alcohols, was developed in this work. The treatment of a cyclic enol carbonate with a Lewis acid in the presence of an allylsilane resulted in the formation of a homoallylic ketone. It was found that the title reaction proceeded well by the combined use of zirconium tetrachloride with allyltrimethylsilane. The allylation occurred with high regioselectivity and the corresponding homoallylic ketones were obtained in good‐to‐high yields. A reaction mechanism involving the decarboxylative formation of an oxyallyl cation equivalent is proposed.
- Subjects
ALLYLATION; CARBON dioxide fixation; ORGANIC chemistry; PROPARGYL alcohol; ENOLS; LEWIS acids; CARBONATES; ALLYL alcohol
- Publication
Helvetica Chimica Acta, 2021, Vol 104, Issue 7, p1
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.202100065