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ChemInform Abstract: Electrophilic 5-endo-trig Cyclizations of 2-Silyl-3-alkenols. A Stereoselective Route to Polysubstituted Tetrahydrofurans.

✍ Scribed by O. ANDREY; L. DUCRY; Y. LANDAIS; D. PLANCHENAULT; V. WEBER

Publisher: John Wiley and Sons
Year: 2010
Weight: 30 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199729099

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✦ Synopsis

Electrophilic 5-endo-trig Cyclizations of 2-Silyl-3-alkenols. A Stereoselective Route to Polysubstituted Tetrahydrofurans. -The scope and limitations of the 5-endo-trig-like cyclization of 9 2-silyl-3-alkenols, e.g. (I), to give tetrahydrofurans, e.g. (III), is investigated. The regioselectivity seems to depend upon the substituent on the olefin and the geometry of the double bond. Styryl systems afford tetrahydrofurans in good yield with complete stereocontrol, whereas olefins of the type (Ie) and (If) favor the formation of selenylated olefins.

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