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Strict base dependence of chirality transfer on [2,3]-Wittig rearrangement of 1,1,2-trifluoroallylic ether

โœ Scribed by Toshiyuki Itoh; Kazutoshi Kudo

Book ID
104211730
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
84 KB
Volume
42
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Investigation of [2,3]-Wittig rearrangement of optically active 1,1,2-trifluoroallylic ether revealed that chirality transfer of the starting compound strictly depended on the base employed, while stereoselectivity of the newly formed olefinic part was controlled with perfect (E)-selectivity. Because the reaction was inhibited by addition of TEMPO; these results suggested [2,3]-Wittig reaction proceeded via a radical pathway mechanism.

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