Organocatalytically Generated Donor − Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2 ‑ a ]quinolines
dc.contributor.author | Sánchez Díez, Eduardo | |
dc.contributor.author | Vesga, Diana L. | |
dc.contributor.author | Reyes Martín, Efraim | |
dc.contributor.author | Uria Pujana, Uxue | |
dc.contributor.author | Carrillo Fernández, María Luisa | |
dc.contributor.author | Vicario Hernando, José Luis | |
dc.date.accessioned | 2018-03-26T08:10:02Z | |
dc.date.available | 2018-03-26T08:10:02Z | |
dc.date.issued | 2016-03-18 | |
dc.identifier.citation | Organic Letters 18(6) : 1270-1273 (2016) | es_ES |
dc.identifier.issn | 1523-7060 | |
dc.identifier.issn | 1523-7052 | |
dc.identifier.uri | http://hdl.handle.net/10810/25991 | |
dc.description.abstract | An easy and straightforward procedure has been developed for the synthesis of highly enantioenriched pyrrolo-[1,2-a]quinolines through a one-pot process that comprises a domino cyclopropane ring opening/aza-Michael/aldol reaction followed by acid-promoted lactamization. The key feature of the synthetic approach relies on the ability of conveniently functionalized cyclopropaneacetaldehydes to undergo organocatalytic activation by a chiral secondary amine that enables the catalytic generation of a donor acceptor cyclopropane. This intermediate has the potential to undergo a ring opening that generates an electrophilic alpha,beta-unsaturated iminium ion that subsequently reacts through the already mentioned domino sequence and in which stereochemical information is very efficiently transferred from the amine catalyst to the final products. Moreover, one of the alkoxycarbonyl moieties can be easily removed by standard hydrolysis/decarboxylation, providing access to the target adducts as single stereoisomers. | es_ES |
dc.description.sponsorship | This research was supported by the Spanish MINECO (FEDER-CTQ2014-52107-P), the Basque Government (Grupos IT328-10), and UPV/EHU (fellowship to E.S. and UFI QOSYC 11/22). Membership in the COST action CM1407 (NatChemDrugs) is also acknowledged. | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | American Chemical Society | es_ES |
dc.relation | info:eu-repo/grantAgreement/MINECO/FEDER-CTQ2014-52107-P | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/3.0/es/ | * |
dc.subject | asymetric-synthesis | es_ES |
dc.subject | alpha,beta-unsaturated aldehydes | es_ES |
dc.subject | formylcyclopropane 1,1 diesters | es_ES |
dc.subject | chiral pyrrolizines | es_ES |
dc.subject | aldol reactions | es_ES |
dc.subject | 3+2 annulation | es_ES |
dc.subject | silyl ethers | es_ES |
dc.subject | derivatives | es_ES |
dc.subject | cycloaddition | es_ES |
dc.subject | construction | es_ES |
dc.title | Organocatalytically Generated Donor − Acceptor Cyclopropanes in Domino Reactions. One-Step Enantioselective Synthesis of Pyrrolo[1,2 ‑ a ]quinolines | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License, which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes. | es_ES |
dc.rights.holder | Atribución-NoComercial-SinDerivadas 3.0 España | * |
dc.relation.publisherversion | https://pubs.acs.org/doi/10.1021/acs.orglett.6b00173 | es_ES |
dc.identifier.doi | 10.1021/acs.orglett.6b00173 | |
dc.departamentoes | Química orgánica II | es_ES |
dc.departamentoeu | Kimika organikoa II | es_ES |
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