Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
The Diels-Alder Reaction Using a Vinyl Sulfoxide Activated by the Participation of a Neighboring Epoxide Group
Hitoshi ABEDaisuke TSUCHIDASetsuko KASHINOYasuo TAKEUCHITakashi HIRAYAMA
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1999 Volume 47 Issue 6 Pages 833-837

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Abstract
A vinyl sulfoxide, which is considered to be a moderately reactive dienophile, could be activated by neighboring participation of an epoxide group. The Diels-Alder reaction of ortho-epoxyphenyl vinyl sulfoxide with cyclopentadiene in the presence of Yb(OTf)3 proceeded smoothly even at room temperature to afford the epoxyopened cycloadducts with moderate stereoselectivity.
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© The Pharmaceutical Society of Japan
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