ORGN 499 |
| Diastereoselective cyclopropanation of allylic alcohol with a gem-dizinc carbenoid and an unusual zinc-boron exchange with B(OMe)3, followed by treatment with excess KHF2 afforded 1,2,3-syn-cis-substituted cyclopropyl trifluoroborates in 58-63% overall yields. These corresponding potassium cyclopropyl trifluoroborates underwent Suzuki-Miyaura cross-coupling reactions to give 1,2,3-functionalized cyclopropanes in good yields. With a subsequent oxidation-epimerization sequence, we also have access to 1,2,3-trans-substituted cyclopropyl trifluoroborate.
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New Reactions, Methodology, Total Synthesis, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, 15 March 2005 Convention Center -- Sails Pavilion, Poster
Sci-Mix
Division of Organic Chemistry |
