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Novel transformation of cyclic 2,4-dienols to 1,5-epoxy-3-en-2-ols. Vanadium-catalyzed epoxidation and rearrangement

✍ Scribed by T. Itoh; K. Jitsukawa; K. Kaneda; S. Teranishi

Publisher
Elsevier Science
Year
1976
Tongue
French
Weight
199 KB
Volume
17
Category
Article
ISSN
0040-4039

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✦ Synopsis

Because of its synthetic utility, increasing interest has been drawn to the highly regio-and stereoselective epoxidation of olefinic alcohols by vanadium catalyst. 1,2) Hitherto, such epoxidation has been believed to occur regioselectively at allylic double bond, without exception.la'lb) In this communication, we report a novel transannular epoxidation of cyclic 2,4-dienols to the bridged oxabicyclic compounds having an u-hydroxy dihydropyran ring.

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