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Palladium-catalyzed reduction of a propargylic acetate derived from a sugar with SmI2. Some unexpected results

✍ Scribed by José Marco-Contelles; Christine Destabel; JoséLuis Chiara

Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 192 KB
Volume: 7
Category: Article
ISSN: 0957-4166
DOI: 10.1016/0957-4166(95)00426-2

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✦ Synopsis

We describe here the unexpected result that we have observed in the palladium-catalyzed reduction of the propargylic acetate 3 derived from a sugar with samarium diiodide. In addition to traces of the expected allene derived product 4, we have obtained mostly a-elimination leading to enynes 5 in moderate yield.

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Palladium-catalyzed reduction of propargylic acetates with SmI2. A mild and convenient method for the preparation of allenes

✍ Takanori Tabuchi; Junji Inanaga; Masaru Yamaguchi 📂 Article 📅 1986 🏛 Elsevier Science 🌐 French ⚖ 230 KB

A highly regioselective reduction of propargylic acetates has been attained by using SmI2 and catalytic Pd(O) in the presence of 2,4-dimethyl-3-pentanol affording various types of allenes in high yields. Allenes not only constitute an important class of natural products but also serve as useful inte