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

Authors
Mahuteau-Betzer, F Ghosez, L
Citation
F. Mahuteau-betzer et L. Ghosez, A [2+2+1] strategy for the conversion of olefins into cyclopentenones. Ring expansion of 2-N-methyl-N-tosyl-cyclobutanones, TETRAHEDR L, 40(28), 1999, pp. 5183-5186
Citations number
27
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
28
Year of publication
1999
Pages
5183 - 5186
Database
ISI
SICI code
0040-4039(19990709)40:28<5183:A[SFTC>2.0.ZU;2-L
Abstract
alpha-N-Methyl-N-tosylcyclobutanones prepared by asymmetric cycloadditions of the corresponding keteniminium triflate to olefins have been converted i nto a mixture of epoxides using dimethylsulfonium ylide. Treatment of these epoxides with lithium iodide unexpectedly yielded the corresponding cyclop entenones. This sequence amounts to a [2+2+1] cyclopentannulation of an ole fin. (C) 1999 Elsevier Science Ltd. All rights reserved.