RT Journal Article
T1 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
A1 Cagiao Marcote, David
A1 Varela Sandá, Iván
A1 Fernández Casado, Jaime
A1 Mascareñas Cid, José Luis
A1 López García, Fernando
AB Piperidine scaffolds are present in a wide range of bioactive natural products and are therefore considered ashighly valuable, privileged synthetic targets. In this manuscript, we describe a gold-catalyzed annulation strategy that allows astraightforward assembly of piperidines and piperidine-containing aza-bridged products from readily available alkene-tetheredoxime 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 thefactors affecting the annulation processes. Moreover, we also describe preliminary experiments demonstrating the viability ofenantioselective versions of the above reactions
PB American Chemical Society
SN 0002-7863
YR 2018
FD 2018
LK http://hdl.handle.net/10347/18461
UL http://hdl.handle.net/10347/18461
LA eng
NO Marcote, D., Varela, I., Fernández-Casado, J., Mascareñas, J., & López, F. (2018). 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. Journal Of The American Chemical Society, 140(48), 16821-16833. doi: 10.1021/jacs.8b10388
NO NOTICE: This is the peer reviewed version of the following article: Marcote, D. C., Varela, I., Fernández-Casado, J., Mascareñas, J.L., López*, F.(2019), Gold(I)–catalyzed enantioselective annulations between allenes and alkene-tethered oxime ethers: A straight entry to highly substitutedpiperidines and aza-bridged medium-sized carbocycles. J. Am. Chem. Soc., 140, 16821-16833 [doi: 10.1021/jacs.8b10388]. This article may beused for non-commercial purposes in accordance with ACS Terms and Conditions for self-archiving
NO This work received financial support from the SpanishMINECO (SAF2016-76689-R, CTQ2017-84767-P, FPUfellowship to I.V. and J.F.-C.), the Xunta de Galicia(ED431C 2017/19, 2015-CP082, Centro Singular de Investigacion de Galicia accreditation 2016-2019 ED431G/09 and ́predoctoral fellowship to D.C.M.), the ERDF, ERC (Adv.Grant No. 340055), and the Orfeo-Cinqa network (CTQ2016-81797-REDC). Dr. Rebeca García-Fandiño is acknowledgedfor her contribution to the DFT studies
DS Minerva
RD 29 abr 2026