949001-65-4Relevant academic research and scientific papers
Gold(I)-Catalyzed Enantioselective Annulations between Allenes and Alkene-Tethered Oxime Ethers: A Straight Entry to Highly Substituted Piperidines and aza-Bridged Medium-Sized Carbocycles
Marcote, David C.,Varela, Iván,Fernández-Casado, Jaime,Mascarenas, José L.,López, Fernando
, p. 16821 - 16833 (2018)
Piperidine scaffolds are present in a wide range of bioactive natural products and are therefore considered as highly valuable, privileged synthetic targets. In this manuscript, we describe a gold-catalyzed annulation strategy that allows a straightforward assembly of piperidines and piperidine-containing aza-bridged products from readily available alkene-tethered oxime ethers (or esters) and N-allenamides. Importantly, we demonstrate the advantages of using oxime derivatives over imines, something pertinent to the whole area of gold catalysis, and provide relevant mechanistic experiments that shed light into the factors affecting the annulation processes. Moreover, we also describe preliminary experiments demonstrating the viability of enantioselective versions of the above reactions.
Carbon-carbon bond formation: Palladium-catalyzed oxidative cross-coupling of N-tosylhydrazones with allylic alcohols
Chen, Huoji,Huang, Li,Fu, Wei,Liu, Xiaohang,Jiang, Huanfeng
, p. 10497 - 10500 (2012/11/06)
In the zone: Pd-catalyzed oxidative cross-coupling of N-tosylhydrazones with allylic alcohols leads to C-C bond formation. A palladium-carbene migratory insertion is proposed to play the key role in this transformation. The reaction proceeds with readily available starting materials to afford substituted alkenes in a highly stereoselective manner (see scheme). Copyright
