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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

AuthorsMarcote, D. C.; Varela, I.; Fernández-Casado, J.; Mascarenas, J. L.; López, Fernando
Issue Date2018
PublisherAmerican Chemical Society
CitationJournal of the American Chemical Society 140: 16821-16833 (2018)
AbstractPiperidine 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.
Publisher version (URL)http://dx.doi.org/10.1021/jacs.8b10388
Identifiersdoi: 10.1021/jacs.8b10388
issn: 0002-7863
e-issn: 1520-5126
Appears in Collections:(IQOG) Artículos
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