Issue 17, 2015

Cerium(iv) ammonium nitrate mediated 5-endo-dig cyclization of α-amino allenylphosphonates to spirodienones

Abstract

α-Amino allenylphosphonates were treated with cerium(IV) ammonium nitrate under various conditions to form spirodienones in good to excellent yields. The 5-endo-dig cyclization proceeds through the formation of a key iminium intermediate. A comprehensive study on the nature of the solvent used for this reaction was undertaken resulting in the formation of three types of spirodienone scaffolds.

Graphical abstract: Cerium(iv) ammonium nitrate mediated 5-endo-dig cyclization of α-amino allenylphosphonates to spirodienones

Supplementary files

Article information

Article type
Communication
Submitted
12 Jan 2015
Accepted
22 Jan 2015
First published
30 Jan 2015

Chem. Commun., 2015,51, 3612-3615

Author version available

Cerium(IV) ammonium nitrate mediated 5-endo-dig cyclization of α-amino allenylphosphonates to spirodienones

P. Adler, A. Fadel and N. Rabasso, Chem. Commun., 2015, 51, 3612 DOI: 10.1039/C5CC00281H

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