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Paper | Special issue | Vol 74, No. 1, 2007, pp.743-761
Published online, 16th November, 2007
DOI: 10.3987/COM-07-S(W)59
Synthesis of Nitrosoalkyl- and Amino-Substituted α,β-Unsaturated Ketones by Cleavage of the N-O-Bond of Bicyclic Δ4-Isoxazolines

Markku Lager, Paul Dietrich, Dirk Weinrich, and Karola Rück-Braun*

*Department of Chemistry, Technical University of Berlin, Strasse des 17. Juni 135, D-10623 Berlin, Germany


The N-O-bond cleavage of bicyclic Δ4-isoxazolines prepared from five-membered cyclic nitrones was studied. Proline-derived bicyclic isoxazolines furnished exclusively acylic nitrosoalkyl-substituted α,β-unsaturated ketones upon treatment with m-CPBA. The nitroso compound 16 was characterized as stable diazo-dioxyde by X-ray analysis. For the N-O-bond cleavage of C3-H-substituted bicyclic Δ4-isoxazolines a Pd(PPh3)4-promoted cleavage protocol in the presence of silanes furnishing enaminones is described.