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Facile synthesis of enantiopure tricyclic furanyl derivatives via tungsten-mediated cycloalkenation reactions and Diels–Alder reactions

✍ Scribed by Heh-Lung Huang; Heh-Chang Huang; Rai-Shung Liu

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
282 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

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-dioxolane substituent of the cycloadducts was degraded to a hydrogen atom to make these molecules possess a common furanyl functionality.

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