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Stereospecific Cyclopropanation of Highly Substituted C-C Double Bonds Promoted by CrCl2. Stereoselective Synthesis of Cyclopropanecarboxamides and Cyclopropyl Ketones
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We describe herein a CrCl2-promoted cyclopropanation of lpha.gif" BORDER=0>,le">-unsaturated amides. This reaction can be carried out on (E)- or (Z)-lpha.gif" BORDER=0>,le">-enamidesin which the C-C double bond is di-, tri-, or tetrasubstituted. In all cases the process is completely stereospecific and only a single diastereoisomeris 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.
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