167751-21-5Relevant academic research and scientific papers
Intramolecular Carbometallation of Organozinc Reagents
Meyer, Christophe,Marek, Ilane,Courtemanche, Gilles,Normant, Jean-F.
, p. 11665 - 11692 (1994)
The intramolecular cyclization reaction of primary or secondary alkenylzincs leads to a cyclopentylmethylzinc derivatives in a totally regiospecific 5-exo-trig cyclization in the presence of a highly sensitive function.
Stereochemistry of the cyclization of alkoxy-substituted 5-hexenyllithiums: Effect of solvent and lithium iodide on diastereoselectivity
Bailey, William F.,Jiang, Xinglong
, p. 3183 - 3194 (2007/10/03)
The stereochemistry of the cyclization of 4-methoxy-5-hexenyllithium, 4-(methoxymethoxy)-5-hexenyllithium, 4-tert-butoxy-5-hexenyllithium, and 3-methoxy-5-hexenyllithium, each of which was generated from the corresponding iodide by low-temperature lithium-iodine exchange, has been studied in a variety of solvent systems. The results of these studies demonstrate that the stereochemical outcome of the cyclizations of alkoxy-substituted 5-hexenyllithiums may be profoundly affected by the medium in which the ring closures are conducted. The etiology of these often dramatic solvent effects is attributed to the ability of certain lithiophilic ligands to competitively complex the lithium iodide salt that is present as a co-product from the exchange reaction used to prepare the organolithiums.
