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ChemInform Abstract: Catalytic Oxyselenenylation—Deselenenylation Reactions of Alkenes — Stereoselective One-Pot Conversion of 3-Alkenols into 2,5-Dihydrofurans.

✍ Scribed by Marcello Tiecco; Lorenzo Testaferri; Claudio Santi

Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Catalytic Oxyselenenylation-Deselenenylation Reactions of Alkenes -Stereoselective One-Pot Conversion of 3-Alkenols into 2,5-Dihydrofurans. -A very simple and convenient synthesis of dihydrofurans (II), (IV) and (VI) is presented involving the diphenyldiselenide-catalyzed stereoselective cyclization of the corresponding methoxycarbonylalkenols (I), (III) and (V), respectively. The method proceeds by an oxyselenenylationdeselenenylation sequence via the corresponding phenylselenotetrahydrofurans [cf. compounds (VIII) and (IX)]. From erythro-alkenols (III) the transdihydrofurans (IV) are obtained stereospecifically, while threo-alkenols (V) exclusively afford cis-dihydrofurans (VI). -(TIECCO, MARCELLO; TESTA-

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