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Efficient Synthesis of Bicyclic Lactones via Tungsten-Mediated Intramolecular Cycloalkenation

✍ Scribed by Liang, Kwei-Wen; Chandrasekharam, Malapaka; Li, Chien-Le; Liu, Rai-Shung

Book ID: 126460013
Publisher: American Chemical Society
Year: 1998
Tongue: English
Weight: 161 KB
Volume: 63
Category: Article
ISSN: 0022-3263
DOI: 10.1021/jo980728m

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Chiral furanyl diene 1 is easily prepared from cycloalkenation of chiral tungsten alkynol with acetaldehyde, followed by demetalation with Me 3 NO. This diene bears a chiral 1,3-dioxolane group to control diastereoselective Diels-Alder reactions with electron-deficient olefins. The chiral 1,3-dioxol