Development of reactions of silacyclopropanes as new methods for stereoselective organic synthesis.
In this Account, we describe the development of stereospecific, stereoselective, regioselective, and chemoselective carbon-carbon bond-forming reactions of silacyclopropanes that occur under mild conditions. By appropriate choice of metal salt catalyst, the regiochemistry of these reactions may be tuned to give the desired product. Stereoselective nucleophilic substitution reactions and stereospecific oxidation of the C-Si bond to a carbon-oxygen bond demonstrate that the products of these reactions serve as useful intermediates for the synthesis of polyoxygenated organic molecules.
Franz
A K
AK
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Woerpel
K A
KA
D002625:Chemistry, Organic; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D055601:Organic Chemistry Phenomena; D017655:Silicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003521:Cyclopropanes; D017655:Silicon Compounds