A mechanistic and synthetic study of organocopper substitution reactions with some homoallylic and cyclopropylcarbinyl substrates: Application to isoprenoid …
GH Posner, JS Ting, CM Lentz
Index: Posner,G.H. et al. Tetrahedron, 1976 , vol. 32, p. 2281 - 2287
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Citation Number: 40
Abstract
The double bond of cholesteryl and 5-norbornen-2-yl tosylates and the cyclopropane ring of cyclopropylmethylcarbinyl tosylate participate in organocuprate substitution reactions; retention of configuration at the nucleofugal sp3-C atom and skeletal reorganizations are observed. A plausible mechanism for these reactions is discussed. Coupling of homogeranyl iodide with a four-carbon, functionalized, vinylic cuprate reagent is applied ...
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