145263-40-7Relevant academic research and scientific papers
A mild, palladium-catalyzed method for the dehydrohalogenation of alkyl bromides: Synthetic and mechanistic studies
Bissember, Alex C.,Levina, Anna,Fu, Gregory C.
, p. 14232 - 14237 (2012/11/06)
We have exploited a typically undesired elementary step in cross-coupling reactions, β-hydride elimination, to accomplish palladium-catalyzed dehydrohalogenations of alkyl bromides to form terminal olefins. We have applied this method, which proceeds in excellent yield at room temperature in the presence of a variety of functional groups, to a formal total synthesis of (R)-mevalonolactone. Our mechanistic studies have established that the rate-determining step can vary with the structure of the alkyl bromide and, most significantly, that L2PdHBr (L = phosphine), an intermediate that is often invoked in palladium-catalyzed processes such as the Heck reaction, is not an intermediate in the active catalytic cycle.
A synthesis of (R)-mevalonolactone
Ray, Nicholas C.,Raveendranath,Spencer, Thomas A.
, p. 9427 - 9432 (2007/10/02)
An enantioselective synthesis of (R)-mevalonolactone (1) has been accomplished starting from known epoxide 2, prepared with ?95% ee by asymmetric epoxidation of nerol. Functional group manipulation of 2 and ozonolysis afforded intermediate 8, which was co
