467426-62-6Relevant articles and documents
Stereospecific cyclopropanation of highly substituted C-C double bonds promoted by CrCl2. Stereoselective synthesis of cyclopropanecarboxamides and cyclopropyl ketones
Concellon, Jose M.,Rodriguez-Solla, Humberto,Mejica, Carmen,Blanco, Elena G.
, p. 2981 - 2984 (2007)
We describe herein a CrCl2-promoted cyclopropanation of α,β-unsaturated amides. This reaction can be carried out on (E)- or (2)-α,β-enamides in which the C-C double bond is di-, tri-, or tetrasubstituted. In all cases the process is completely stereospecific and only a single diastereoisomer is obtained. In addition, cyclopropyl ketones were readily prepared by reaction of the cyclopropanecarboxamides (derived from morpholine) obtained with a range of organolithium compounds. A mechanism has been proposed to explain the cyclopropanation reaction.