Synthesis 1990; 1990(1): 32-34
DOI: 10.1055/s-1990-26778
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A Novel Acetonylation of Carbonucleophiles via Palladium-Catalyzed Allylation with Isopropyl 2-Methylene-3,5-dioxahexyl Carbonate

Isao Ikeda* , Xue-Ping Gu, Toshio Okuhara, Mitsuo Okahara
  • *Department of Applied Chemistry, Faculty of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565, Japan
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Publication History

Publication Date:
17 September 2002 (online)

Carbonucleophiles such as malonate esters, ß-keto esters, phenylacetate ester, and phenylacetonitrile were acetonylated in high yields by allylation with isopropyl (or methyl) 2-methylene-3,5-dioxahexyl carbonate (4b or 4a) in the presence of palladium-phosphine catalyst under neutral conditions, followed by acidic hydrolysis. Adopting this procedure dihydrojasmone (7) was prepared from ethyl 3-oxononanoate (6) in an overall yield of 72%.