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

Mahuteau-Betzer, Florence;Ghosez, Léon
(1999) Tetrahedron Letters — Vol. 40, n° 28, p. 5183-5186 (1999)

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  • Mahuteau-Betzer, FlorenceUCLouvain
    Author
  • Ghosez, LéonUCLouvain
    Author
Abstract
alpha-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. (C) 1999 Elsevier Science Ltd. All rights reserved.
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Mahuteau-Betzer, F., & Ghosez, L. (1999). A [2+2+1] strategy for the conversion of olefins into cyclopentenones. Ring expansion of 2-N-methyl-N-tosyl-cyclobutanones. Tetrahedron Letters, 40(28), 5183-5186. https://doi.org/10.1016/S0040-4039(99)00948-X (Original work published 1999)