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A [2+2+1] strategy for the conversion of olefins into cyclopentenones. Ring expansion of 2-N-methyl-N-tosyl-cyclobutanones

✍ Scribed by Florence Mahuteau-Betzer; Léon Ghosez

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
246 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

ec-N-Methyl-N-tosylcyclobutanones prepared by asymmetric cycloadditions of the corresponding keteniminium triflate to olefins have been converted into a mixture of epoxides using dimethylsulfonium ylide. Treatment of these epoxides with lithium iodide unexpectedly yielded the corresponding cyclopentenones. This sequence amounts to a [2+2+1] cyclopentannulation of an olefin.

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